intramolecular cycloaddition of azomethine ylides ...10.1007/s10593-016-1912... · chemistry of...
TRANSCRIPT
Chemistry of Heterocyclic Compounds 2016, 52(7), 484–492
Intramolecular cycloaddition of azomethine ylides activated by aromatic rings: scope and limitations
Hongxiang Xie1, Bowen Gong1, Xinran Zhong1, Hongming Cui1, Jinbao Xiang1*
SUPPLEMENTARY INFORMATION
Combinatorial Chemistry and Drug Discovery of Jilin University, The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Road, Changchun, Jilin 130021, P. R. China; е-mail: [email protected]
1 Voronezh State University,
1 Universitetskaya Sq., Voronezh 394006, Russia; e-mail: [email protected] 2 People's Friendship University of Russia,
6 Miklukho-Maklaya St., Moscow 117198, Russia; e-mail: [email protected]
S2
Spectra
8.9
41
8.8
47
7.2
72
4.8
52
2.7
59
0.0
00
3.00
1.42
1.12 1.19
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j322-88.fidBOXD-PNO2 May 6 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 4PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1794.04 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -51.83 B = 104.91
Fig. S-1: 1H Spectra of compound 3.1
S3
8.4
96
8.0
11
7.2
68 5
.954
5.9
19 5
.897
5.8
63 5
.244
5.2
40 5
.235
5.2
30 5
.210
5.2
06 5
.200
5.1
94 5
.190
5.1
43 5
.138
4.5
73 4
.558
4.3
04 4
.297
4.2
93 4
.288
4.2
82 4
.277
3.2
40 3
.222
2.9
43
-0.
000
0.94 0.92 0.72
1.86 2.10 2.03
3.00
1.25
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j322-94.fidBOXD-PNO2 May 17 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1792.96 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -31.43 B = 90.86
Fig. S-2: 1H Spectra of compound 4.1
161
.995
156
.919
156
.507
133
.632
117
.331
116
.544
77.
623
77.
200
76.
773
60.
978
54.
128
37.
593
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$J322-94C.fidJ322-94C May 20 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 128PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6827.81 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -160.55 B = 277.23
Fig. S-3: 13C Spectra of compound 4.1
S4
10.
325
7.2
69
5.8
99 5
.863
5.8
41 5
.827
5.8
08 5
.279
5.2
75 5
.270
5.2
66 5
.260
5.2
55 5
.251
5.2
44 5
.241
5.2
36 5
.233
5.2
09 5
.204
5.1
99 5
.194
4.3
04 4
.298
4.2
95 4
.284
4.2
79 4
.276
2.8
86 2
.527
2.5
16 2
.507
-0.
000
-0.
011
0.57
1.00
2.02 2.24
3.39 3.00
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j444-29.fidBOXD-PNO2 Sep 7 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1793.61 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = 24.50 B = 20.05
Fig. S-4: 1H Spectra of compound 5.2
187
.217
168
.102
164
.713
132
.245
118
.674
107
.723
77.
631
77.
200
76.
772
54.
591
39.
991
26.
057
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j444-29-20110909-c.fidWROZ Sep 9 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 96PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6830.67 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -164.29 B = 289.76
Fig. S-5: 13C Spectra of compound 5.2
S5
10.
385
8.4
21 8
.416
8.4
09 8
.401
8.3
94 8
.388
7.5
24 7
.514
7.5
07 7
.502
7.4
95 7
.491
7.4
86 7
.475
7.4
71 7
.467
7.4
45 7
.437
7.2
60 5
.992
5.9
59 5
.933
5.9
20 5
.900
5.8
81 5
.308
5.3
03 5
.300
5.2
97 5
.292
5.2
67 5
.262
5.2
59 5
.255
5.2
49 5
.245
4.4
16 4
.412
4.4
07 4
.396
4.3
92 4
.387
2.9
73 1
.578
0.0
11 -
0.00
0 -
0.01
1
0.59
1.59
2.68
0.68
1.88 2.00
3.03
15 10 5 0 PPM
E:\NMR_NUTS\DATA\$j420-81.fidBOXD-PNO2 Sep 15 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 16PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1791.41 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -24.26 B = 82.33
Fig. S-6: 1H Spectra of compound 5.3
187
.230
165
.541
163
.290
161
.739
135
.882
132
.360
132
.048
129
.218
128
.570
118
.763
108
.342
77.
622
77.
200
76.
778
54.
874
40.
091
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j420-81-20110920.fidJ338-85-1C Sep 20 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 208PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6829.31 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -161.64 B = 273.16
Fig. S-7: 13C Spectra of compound 5.3
S6
7.2
69
7.2
67
5.9
78 5
.941
5.9
23 5
.886
5.3
02 5
.282
5.2
49 5
.225
4.6
40
4.2
21 4
.204
3.1
62
2.4
75
2.0
79
-0.
000
0.81
2.14 2.06 2.08
3.09 3.00
1.49
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j420-66.fidBOXD-PNO2 Sep 8 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 4PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1794.27 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -4.76 B = 51.34
Fig. S-8: 1H Spectra of compound 4.2
165
.603
165
.047
161
.899
133
.779
117
.109
110
.871
77.
634
77.
200
76.
788
58.
197
55.
311
38.
110
25.
505
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j420-66-20110915.fidZJ-0718C Sep 15 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 208PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6829.84 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -163.42 B = 274.63
Fig. S-9: 13C Spectra of compound 4.2
S7
8.3
87
8.3
81 8
.369
8.3
65 8
.356
7.4
60 7
.453
7.4
43 7
.436
7.4
23 7
.260
6.0
48 6
.031
6.0
10 5
.993
5.9
73 5
.955
5.3
31 5
.327
5.3
09 5
.305
5.2
72 4
.704
4.3
03 4
.286
3.2
80 3
.266
1.9
52
0.0
12 -
0.00
0
2.01
0.82
1.96 2.00 2.04
3.14 2.96
1.49
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j420-82.fidBOXD-PNO2 Jul 28 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 4PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1790.91 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -29.70 B = 89.88
Fig. S-10: 1H Spectra of compound 4.3
165
.113
162
.843
161
.819
136
.839
133
.796
130
.968
128
.445
128
.388
117
.267
111
.691
77.
621
77.
200
76.
777
58.
622
55.
457
38.
229
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j420-82-c-20110909.fidWROZ Sep 9 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 176PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6829.31 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -168.55 B = 290.08
Fig. S-11: 13C Spectra of compound 4.3
S8
8.5
36
8.1
11
7.2
69
5.9
60 5
.944
5.9
41 5
.925
5.9
20 5
.908
5.9
04 5
.886
5.8
68 5
.853
5.2
41 5
.235
5.2
31 5
.223
5.2
17 5
.212
5.2
06 5
.201
5.1
96 5
.190
5.1
66 5
.161
5.1
54 4
.321
4.3
16 4
.309
4.3
04 4
.299
4.2
94 3
.615
3.1
73 2
.456
2.1
59 2
.076
0.0
10 0
.000
0.77
2.18 2.04
0.83
2.02
2.99 3.03
2.00
0.90
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j322-95.fidBOXD-PNO2 May 20 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1793.11 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -23.63 B = 89.39
Fig. S-12: 1H Spectra of compound 7b
Fig. S-13: 13C Spectra of compound 7b
S9
7.2
57
5.9
71 5
.954
5.9
38 5
.913
5.8
95 5
.879
5.2
77 5
.271
5.2
63 5
.257
5.2
53 5
.224
5.2
18 5
.214
4.2
84 4
.279
4.2
73 4
.268
3.5
54 3
.117
2.4
56 2
.452
1.6
40
0.0
05 -
0.00
7
0.72
1.89 2.01 1.96
3.00
5.84
10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j420-69.fidBOXD-PNO2 Sep 6 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1791.10 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -10.91 B = 67.76
Fig. S-14: 1H Spectra of compound 7c
165
.557
165
.018
161
.408
134
.411
116
.650
111
.136
77.
619
77.
200
76.
770
55.
381
49.
202
37.
659
36.
666
25.
583
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j420-69-c-20110909.fidWROZ Sep 9 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 112PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6829.14 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -147.77 B = 254.37
Fig. S-15: 13C Spectra of compound 7c
S10
8.3
82
8.3
75 8
.364
8.3
60 8
.357
8.3
51 8
.349
7.4
61 7
.455
7.4
47 7
.440
7.4
29 7
.424
7.4
18 7
.412
7.2
60 6
.045
6.0
27 6
.010
5.9
87 5
.970
5.9
53 5
.336
5.3
29 5
.325
5.3
18 5
.297
5.2
92 5
.286
5.2
81 5
.272
5.2
67 5
.262
5.2
57 5
.251
4.3
67 4
.363
4.3
57 4
.352
3.6
45 3
.253
3.2
42 2
.489
1.7
64 0
.010
-0.
000
-0.
013
1.75
3.09
0.79
1.99 2.06 2.09
3.00 2.98
1.21
12 10 8 6 4 2 0 PPM Fig. S-16: 1H Spectra of compound 7d
165
.627
162
.289
161
.271
137
.094
134
.464
130
.722
128
.350
128
.321
116
.821
112
.206
77.
628
77.
200
76.
772
55.
525
49.
452
37.
802
36.
765
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j420-85-20110901.fidWW-40C Sep 1 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 432PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6829.14 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -152.00 B = 253.92
Fig. S-17: 13C Spectra of compound 7d
S11
10.
235
8.2
70
7.2
70 5
.928
5.8
92 5
.872
5.8
36 5
.251
5.2
48 5
.242
5.2
39 5
.231
5.2
26 5
.222
5.2
17 5
.213
5.2
09 5
.205
5.1
76 5
.170
5.1
65 4
.268
4.2
62 4
.259
4.2
49 4
.245
4.2
40 4
.038
2.9
20
0.0
00
3.00
2.06
2.89
0.58 0.73
2.02
0.59
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j444-20.fidBOXD-PNO2 Sep 2 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1795.03 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -26.46 B = 93.02
Fig. S-18: 1H Spectra of compound 6.1
186
.605
172
.816
158
.415
136
.959
132
.893
118
.084
99.
535
77.
628
77.
200
76.
768
54.
662
54.
493
39.
875
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j444-20-c.fidliufm-249C Sep 7 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 224PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6832.69 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -175.64 B = 301.67
Fig. S-19: 13C Spectra of compound 6.1
N
N O
O
N
N
N O
O
N
S12
9.7
82
8.6
24
7.7
45 7
.741
7.7
36 7
.727
7.7
20 7
.713
7.5
55 7
.552
7.5
38 7
.532
7.5
24 7
.518
7.5
12 7
.505
7.4
92 7
.488
7.4
77 7
.263
5.9
82 5
.964
5.9
51 5
.944
5.9
31 5
.923
5.9
12 5
.893
5.8
72 5
.308
5.3
03 5
.299
5.2
72 5
.267
5.2
63 5
.258
5.2
54 5
.249
5.2
43 5
.238
4.3
93 4
.389
4.3
83 4
.374
4.3
69 4
.363
3.0
79 3
.070
1.3
47 1
.263
1.2
39 0
.011
0.0
00 -
0.01
1
0.68 0.58
1.88
2.77
0.62
1.81 1.95
3.00
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j444-49.fidBNBC-t8 Sep 23 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1792.23 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -23.43 B = 83.44
Fig. S-20: 1H Spectra of compound 6.3
188
.474
173
.019
161
.158
158
.144
136
.897
132
.510
130
.840
128
.658
118
.456
111
.270
77.
626
77.
200
76.
770
54.
508
39.
851
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j444-49-20110927.fidLHM-110707C Sep 27 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 224PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6827.89 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -150.51 B = 245.47
Fig. S-21: 13C Spectra of compound 6.3
S13
8.
278
7.
268
5.
994
5.
978
5.
961
5.
944
5.
920
5.
903
5.
886
5.
870
5.
290
5.
284
5.
277
5.
247
5.
241
5.
233
5.
226
5.
213
5.
207
5.
202
4.
153
4.
142
3.
944
3.
522
3.
048
2.
450
2.
163
0.
000
0.49 0.66
1.82 2.05
2.81
1.94
2.97 3.00
1.26
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j444-39.fidaih-33 Sep 19 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secPTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1793.35 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -36.68 B = 110.24
Fig. S-22: 1H Spectra of compound 7e
169
.278
165
.679
155
.004
134
.878
116
.467
101
.412
77.
623
77.
200
76.
764
55.
896
53.
941
46.
399
37.
731
36.
826
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j444-39-c-20110921.fidLQW-0920C Sep 21 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 208PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6832.44 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -158.84 B = 271.43
Fig. S-23: 13C Spectra of compound 7e
N
N
N
NH
O
N
N
N
NH
O
S14
8.2
84
7.5
39 7
.525
7.5
14 7
.507
7.4
96 7
.427
7.4
17 7
.413
7.4
02 7
.395
7.2
70 6
.000
5.9
82 5
.965
5.9
42 5
.925
5.9
08 5
.306
5.3
02 5
.275
5.2
70 5
.245
5.2
41 4
.272
4.2
55
3.6
83
3.0
95
2.5
15
1.5
69
0.0
00
0.66 0.80
1.96 2.06 2.02
3.10 3.00
1.16
1.77
2.60
10 8 6 4 2 0PPM
C:\NMR_NUTS\DATA\$j339-74B.fidANB-12 Jan 17 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6002.40 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1803.47 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -35.33 B = 78.04
Fig. S-24: 1H Spectra of compound 7f
168
.10
1
163
.85
5
155
.30
1
134
.91
7 1
34.5
27
129
.61
8 1
29.0
41
128
.78
3 1
16.4
34
113
.80
2
77
.61
4 7
7.2
00
76
.76
6
55
.53
5 4
9.2
87
37
.52
8 3
6.7
22
200 150 100 50 0 PPM
C:\NMR_NUTS\DATA\$j339-74bc.fidxxx10 Jan 15 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 128PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6816.32 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -176.13 B = 288.64
Fig. S-25: 13C Spectra of compound 7f
N
N
N
SPh
NH
N
N
N
SPh
NH
S15
8.5
97
7.4
50 7
.266
6.0
22 5
.971
5.9
31 5
.896
5.3
08 5
.302
5.2
69 5
.265
5.2
51 5
.245
5.2
40 5
.236
4.2
81 4
.264
3.5
67
3.1
41
2.1
54 2
.133
1.4
82
-0.
000
0.51 0.68
1.87 1.95 2.01
2.95 3.00
1.32
4.56
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j444-54.fid4-py6-cg Sep 28 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1793.52 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -25.36 B = 91.81
Fig. S-26: 1H Spectra of compound 7g
167
.101
165
.223
155
.449
139
.701
134
.411
128
.889
128
.547
128
.475
117
.016
115
.481
77.
630
77.
200
76.
793
55.
672
49.
407
38.
033
35.
998
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j444-54-1012.fidtx111011 Oct 12 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 640PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6834.28 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -152.79 B = 257.35
Fig. S-27: 13C Spectra of compound 7g
S16
10.
334
7.3
31 7
.304
7.2
76 7
.264
6.9
78 6
.974
6.9
48
5.9
43 5
.923
5.9
09 5
.904
5.8
90 5
.884
5.8
71 5
.850
5.3
01 5
.256
5.2
51 5
.218
5.2
13 5
.208
5.2
03 5
.197
3.7
43 3
.724
2.8
27
1.5
94
0.0
69 0
.000
0.44 0.61
1.83 2.00
3.22
1.46
1.10
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j420-9.fidEF Jun 8 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1792.01 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -42.68 B = 106.08
Fig. S-28: 1H Spectra of compound 10.3
189
.351
155
.433
137
.083
133
.679
133
.609
123
.600
122
.138
118
.217
117
.304
77.62
6
77.20
0
76.78
1
60.48
0
41.15
1
200 150 100 50 0 PPM
E:\NMR_NUTS\data\$j420-28-c.fidwyp-24C Jan 7 2012USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 144PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6823.58 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -155.19 B = 280.40
Fig. S-29: 13C Spectra of compound 10.3
O
Cl
N
O
Cl
N
S17
10.
399
7.5
68 7
.557
7.5
51 7
.546
7.5
42 7
.537
7.4
39 7
.437
7.4
31 7
.428
7.4
25 7
.421
7.4
15 7
.411
7.4
06 7
.262
7.1
95 7
.168
7.1
41 6
.858
6.4
21 6
.394
5.9
59 5
.937
5.9
04 5
.881
5.8
47 5
.826
5.3
03 5
.297
5.2
52 5
.248
5.2
46 5
.241
5.2
19 3
.721
3.7
02 2
.839
2.8
24
-0.
000
0.64 0.76 0.63 0.63
1.74 1.90
3.00
1.67
2.49
0.86
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j420-55.fidBOXD-PNO2 Sep 15 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1792.01 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -8.59 B = 61.67
Fig. S-30: 1H Spectra of compound 10.4
191
.239
157
.597
144
.564
135
.549
133
.950
133
.248
132
.433
129
.708
129
.131
124
.509
120
.245
118
.193
115
.325
77.
624
77.
200
76.
791
62.
078
41.
507
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j444-55.fidJ338-85-1C Sep 20 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 80PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6824.09 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -159.68 B = 283.91
Fig. S-31: 13C Spectra of compound 10.4
S18
8.1
95
8.1
88 8
.179
8.1
73 7
.626
7.6
20 7
.601
7.5
94 7
.303
6.8
87 6
.872
6.8
63 6
.847
5.9
36 5
.913
5.8
79
5.3
10 5
.306
5.2
54 5
.248
5.2
01 5
.195
5.1
67 5
.161
3.7
66 3
.761
3.7
47 3
.741
3.7
24
2.8
15 2
.770
2.4
41 2
.431
1.8
10
0.0
00
0.53 0.73
1.80 2.02 1.86
2.90 3.00
1.18
0.75 0.72
10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j420-95.fidBOXD-PNO2 Aug 31 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1804.27 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -24.97 B = 101.51
Fig. S-32: 1H Spectra of compound 11a
161
.862
146
.037
138
.018
135
.426
126
.013
117
.347
116
.846
77.
627
77.
200
76.
771
57.
665
52.
006
38.
882
36.
179
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j420-95-20110914.fidWROZ Sep 14 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 208PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6828.27 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -165.14 B = 278.45
Fig. S-33: 13C Spectra of compound 11a
S19
7.3
27
7.3
22 7
.303
7.2
98 7
.261
7.2
46 7
.242
7.2
21 7
.216
7.1
97 7
.190
7.1
25 7
.121
7.0
98 7
.095
7.0
72 7
.068
7.0
48 7
.044
7.0
23 7
.020
5.9
14 5
.880
5.8
56 5
.822
5.2
80 5
.275
5.2
70 5
.263
5.2
23 5
.217
5.2
13 5
.207
5.1
80 5
.176
5.1
71 5
.167
5.1
42 5
.137
5.1
32 3
.804
3.5
04 3
.483
2.6
56 2
.434
1.7
95 0
.000
0.64
1.66
1.24
1.86 1.80
2.94 3.00
2.09
1.49
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j322-30.fidKLC-100-4 Mar 9 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 5995.20 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1801.65 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -34.22 B = 66.42
Fig. S-34: 1H Spectra of compound 11b
152
.104
135
.455
134
.603
129
.932
127
.698
123
.653
120
.722
117
.185
77.
631
77.
200
76.
783
60.
497
52.
158
41.
532
35.
843
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j322-30C.fidmyh-H Mar 11 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 240PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6823.92 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -170.38 B = 281.70
Fig. S-35: 13C Spectra of compound 11b
S20
7.2
62
7.1
70 7
.144
7.1
17 7
.100
7.0
94 7
.074
7.0
68 7
.020
7.0
15 6
.994
6.9
90 5
.914
5.8
80 5
.857
5.8
43 5
.837
5.8
22 5
.803
5.2
99 5
.296
5.2
91 5
.285
5.2
80 5
.238
5.2
34 5
.227
5.2
23 5
.201
5.1
97 5
.192
5.1
87 5
.167
5.1
63 5
.158
5.1
53 3
.943
3.5
97 3
.579
2.6
78 2
.446
2.4
33 2
.299
2.2
83 1
.254
0.0
11 -
0.00
0
0.59
1.69
3.00 2.98
1.22
1.92 1.96
1.49
0.79
10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j420-80.fidBOXD-PNO2 Sep 9 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1791.92 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -26.20 B = 96.18
Fig. S-36: 1H Spectra of compound 11c
154
.498
135
.777
135
.203
132
.709
128
.379
124
.537
119
.239
117
.330
77.
630
77.
200
76.
777
60.
790
48.
667
41.
433
36.
061
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j420-80-20110914.fidWROZ Sep 14 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 112PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6810.36 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -150.79 B = 252.05
Fig. S-37: 13C Spectra of compound 11c
N
NH
Cl
N
NH
Cl
S21
7.3
09
7.2
90 7
.284
7.2
79 7
.262
7.2
55 7
.239
7.2
35 7
.233
7.2
07 7
.176
7.1
49 7
.123
7.0
72 7
.067
7.0
45 7
.040
7.0
20 7
.016
6.9
96 6
.991
5.9
53 5
.875
5.8
42 5
.292
5.2
87 5
.235
5.2
29 5
.197
5.1
90 5
.162
5.1
57 4
.009
3.6
06 3
.585
2.6
94 2
.414
1.2
55
0.0
11 0
.000
0.69
1.78 2.04 2.00
3.47 3.30 3.63
1.73
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j420-75.fidBOXD-PNO2 Jul 25 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 4PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1790.98 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -0.10 B = 62.59
Fig. S-38: 1H Spectra of compound 11d
153
.893
136
.677
136
.345
135
.607
130
.268
129
.273
128
.183
126
.709
120
.161
117
.183
77.
607
77.
200
76.
780
61.
045
49.
297
41.
584
36.
418
200 150 100 50 0 PPM
E:\NMR_NUTS\data\$j420-75-20111020.fidJ340-88-bc Oct 20 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 224PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6828.60 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -156.57 B = 258.71
Fig. S-39: 13C Spectra of compound 11d
S22
7.2
63
7.2
29 7
.201
6.6
61 6
.599
6.5
92 6
.572
6.5
65 5
.909
5.8
88 5
.873
5.8
52 5
.836
5.8
18 5
.798
5.2
72 5
.214
5.1
78 5
.144
3.7
88 3
.742
3.5
01 3
.482
2.6
45
2.4
16 2
.230
2.1
86 2
.043
1.2
56
0.0
00
0.81
1.79 1.91
2.96 3.04
1.35
3.03
1.88
0.90 0.90 0.91
10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j444-12.fidBOXD-PNO2 Aug 22 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 4PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1792.42 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -39.06 B = 114.59
Fig. S-40: 1H Spectra of compound 11e
159
.370
153
.397
135
.484
130
.868
126
.889
117
.242
107
.737
107
.530
77.
626
77.
200
76.
807
60.
509
55.
318
51.
930
41.
372
36.
013
200 150 100 50 0 PPM Fig. S-41: 13C Spectra of compound 11e
S23
8.
277
8.
267
8.
074
8.
065
8.
045
8.
035
7.
265
7.
246
7.
017
6.
987
5.
919
5.
885
5.
862
5.
828
5.
323
5.
317
5.
312
5.
276
5.
271
5.
266
5.
259
5.
255
5.
242
5.
237
5.
233
3.
781
3.
764
3.
745
2.
835
2.
818
2.
468
2.
450
1.
708
0.
000
-0.
011
-0.
019
0.82 0.78 0.89 0.76
1.88
4.06
3.20 3.10
1.58
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j420-89.fidaih-33 Sep 19 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secPTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1792.71 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -21.24 B = 85.26
Fig. S-42: 1H Spectra of compound 11f
157
.581
141
.661
134
.151
132
.874
125
.893
123
.447
118
.353
117
.895
77.
611
77.
200
76.
776
59.
206
52.
198
40.
170
36.
459
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j420-89-20110921.fidLQW-0920C Sep 21 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 384PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6830.87 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -156.60 B = 264.49
Fig. S-43: 13C Spectra of compound 11f
S24
8.
524
7.
939
7.
384
7.
362
7.
355
7.
338
7.
311
7.
306
7.
288
7.
276
7.
269
7.
263
7.
248
7.
244
4.
157
4.
137
4.
131
4.
109
3.
980
3.
962
3.
423
3.
381
3.
352
3.
339
3.
320
3.
177
2.
689
2.
662
2.
633
2.
615
2.
353
2.
286
2.
261
2.
214
2.
168
2.
033
0.
000
0.58 0.70 0.82 0.86
1.81
2.66
0.87
2.33
3.00
4.72
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j322-96-1.fidBOXD-PNO2 May 23 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1793.10 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -16.37 B = 67.64
Fig. S-44: 1H Spectra of compound 8b
160
.114
157
.566
154
.798
142
.618
128
.456
127
.428
112
.041
77.
632
77.
200
76.
771
65.
269
60.
003
51.
710
37.
459
36.
046
35.
161
34.
132
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j322-96-1C.fidWJ-0523C May 27 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 480PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6829.51 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -156.37 B = 272.19
Fig. S-45: 13C Spectra of compound 8b
S25
7.4
77
7.4
56 7
.451
7.4
28 7
.425
7.4
21 7
.375
7.3
40 7
.319
7.2
63 7
.255
4.5
28
4.3
07 4
.290
4.2
73 4
.260
3.4
65 3
.447
3.4
29 3
.291
3.2
72 3
.264
3.2
54 3
.218
3.1
54 3
.143
2.5
11 2
.502
2.4
77 2
.467
2.4
45 2
.396
2.3
48 2
.262
2.2
36 2
.214
2.1
24 1
.253
1.2
13 1
.163
0.8
80 0
.011
-0.
000
-0.
010
-0.
044
-0.
046
0.79 0.66 0.80
4.00 4.08
1.63
2.95
4.59
10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j444-57.fidBOXD-PNO2 Oct 10 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1791.98 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -28.29 B = 89.30
Fig. S-46: 1H Spectra of compound 8c
166
.341
160
.652
159
.180
142
.844
129
.832
128
.490
128
.265
127
.368
77.
624
77.
200
76.
778
64.
981
58.
405
51.
032
37.
906
36.
537
35.
742
33.
455
25.
804
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$J444-57C.fid1.4 Oct 13 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 1056PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6809.21 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -157.59 B = 262.88
Fig. S-47: 13C Spectra of compound 8c
N
N
N
NCl
H
H
N
N
N
NCl
H
H
S26
8.4
14
8.4
07 8
.396
8.3
81
7.4
52 7
.443
7.4
36 7
.433
7.4
29 7
.380
7.3
76 7
.355
7.3
46 7
.323
7.2
56
4.6
08 4
.593
4.2
68
3.3
43
2.4
86 2
.247
2.2
22 2
.157
0.0
00
1.92
0.88 0.79 0.74 0.85
8.01
3.00 2.74
1.25 1.57
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\DATA\$j420-88.fidBOXD-PNO2 Aug 19 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1790.36 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -1.39 B = 45.28
Fig. S-48: 1H Spectra of compound 8d
162
.365
160
.827
160
.071
143
.436
137
.401
130
.692
128
.538
128
.328
128
.217
127
.304
106
.710
77.
628
77.
200
76.
774
65.
257
58.
500
51.
248
38.
183
36.
658
35.
846
33.
722
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$J420-88C.fidWW-40C Sep 1 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 1296PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6828.43 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -151.35 B = 251.62
Fig. S-49: 13C Spectra of compound 8d
S27
8.
273
7.
389
7.
364
7.
341
7.
327
7.
305
7.
280
7.
262
4.
420
4.
405
4.
178
3.
886
3.
358
3.
322
3.
234
3.
216
3.
194
3.
173
2.
481
2.
466
2.
448
2.
282
2.
259
2.
233
2.
192
2.
164
2.
149
2.
118
2.
032
1.
255
-0.
000
0.50 0.83 0.80
3.00
0.76 0.64
3.46
1.20 0.99 1.00
3.36
4.82
10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j444-46.fidLQW-0920H Sep 20 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1792.42 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -13.83 B = 56.02
Fig. S-50: 1H Spectra of compound 8e
167
.458
161
.329
156
.109
143
.220
128
.473
128
.382
128
.003
127
.206
77.
621
77.
200
76.
774
65.
526
55.
857
53.
432
51.
657
38.
135
36.
678
35.
772
33.
791
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j444-46-20110923.fidCTA-C Sep 23 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 208PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6829.30 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -158.65 B = 265.65
Fig. S-51: 13C Spectra of compound 8e
S28
8.2
84
7.5
26 7
.524
7.5
17 7
.512
7.5
01 7
.496
7.4
27 7
.424
7.4
21 7
.409
7.3
97 7
.393
7.3
89 7
.379
7.3
72 7
.365
7.3
60 7
.314
7.3
06 7
.295
7.2
70 5
.306
4.6
05 4
.591
4.2
63 3
.492
3.4
14 3
.312
3.2
92 3
.225
3.2
01 2
.496
2.2
47 2
.050
1.2
62
0.0
11 0
.000
-0.
011
0.65 0.90 0.86 0.87 0.82 0.99
3.00
4.95
2.00
6.91
0.74
10 8 6 4 2 0 PPM
C:\NMR_NUTS\DATA\$j339-75.fidANB-12 Jan 17 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6002.40 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1803.58 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -35.36 B = 62.24
Fig. S-52: 1H Spectra of compound 8f
165
.94
6
158
.61
8 1
56.6
36
143
.68
5 1
34.8
22
130
.51
1 1
29.8
46
129
.07
6 1
28.6
48
128
.53
1 1
27.9
45
127
.18
2
77
.61
9 7
7.2
00
76
.77
6 6
5.7
17
58
.82
7 5
1.0
76
38
.37
7 3
6.7
83
36
.55
1 3
4.0
90
200 150 100 50 0 PPM
C:\NMR_NUTS\DATA\$j339-75-1c.fidYZD-126 Jan 21 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 592PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6825.31 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -161.00 B = 272.63
Fig. S-53: 13C Spectra of compound 8f
N
N
N
NS
H
H
N
N
N
NS
H
H
S29
8.6
21
7.9
15 7
.893
7.4
97 7
.493
7.4
86 7
.480
7.4
66 7
.453
7.4
44 7
.427
7.4
23 7
.407
7.3
38 7
.334
7.3
29 7
.311
7.3
06 7
.286
7.2
73 7
.262
7.2
56 7
.230
7.2
08 4
.519
4.5
08 4
.133
4.1
10 4
.086
3.4
01 3
.382
3.3
59 3
.335
3.2
65 3
.231
2.5
07 2
.495
2.2
60 2
.234
2.2
16 2
.191
2.0
25 1
.952
1.2
59 1
.253
0.0
00 -
0.00
6 -
0.01
1 -
0.03
5
0.91 0.88
1.74
3.21
0.88 1.00
4.48
0.61
1.83
2.97
6.11
10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j444-56.fidBOXD-PNO2 Oct 11 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1791.56 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -27.87 B = 82.75
Fig. S-54: 1H Spectra of compound 8g
163
.251
160
.385
156
.852
144
.518
138
.391
129
.398
128
.986
128
.411
128
.109
127
.122
126
.971
108
.010
77.
622
77.
200
76.
776
67.
108
58.
888
51.
218
39.
753
38.
598
36.
742
35.
148
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j444-56-20111014.fidZQ-1.3 Oct 14 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 256PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6825.92 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -148.22 B = 240.17
Fig. S-55: 13C Spectra of compound 8g
S30
8.1
20
8.1
14 8
.102
8.0
96 7
.361
7.3
33 7
.324
7.3
13 7
.280
7.2
71 7
.261
7.2
57 7
.238
7.2
33 6
.562
6.5
46 6
.537
6.5
22
4.1
15 4
.094
3.9
51 3
.927
3.9
02 3
.245
3.2
26 3
.098
2.8
67 2
.854
2.8
34 2
.814
2.7
94 2
.268
2.2
52 2
.244
2.2
26 2
.220
2.0
23
0.0
00 -
0.00
7
3.00
1.94
0.96
2.72
1.84
0.86 0.85 0.69
3.69
0.67 0.82
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j420-98-1.fidgc-3 Aug 11 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 4PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1790.92 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -31.07 B = 96.76
Fig. S-56: 1H Spectra of compound 12a
158
.451
146
.905
142
.626
138
.352
128
.317
128
.232
127
.194
115
.470
111
.654
77
.624
77
.200
76
.770
66
.100
62
.618
53
.646
38
.254
37
.324
35
.780
35
.681
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j444-55-20110928.fidJD-SeD2-C Sep 28 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 112PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6822.19 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -146.84 B = 242.65
Fig. S-57: 13C Spectra of compound 12a
S31
7.3
60
7.3
56 7
.349
7.3
32 7
.327
7.3
18 7
.309
7.2
90 7
.279
7.2
74 7
.267
7.2
60 7
.255
7.2
22 7
.217
7.1
93 7
.171
7.1
64 7
.097
7.0
91 7
.071
7.0
66 6
.759
6.7
49 6
.730
6.7
25 6
.700
6.6
98 4
.144
4.1
23 3
.921
3.8
98 3
.875
3.0
65 3
.044
3.0
29 3
.020
3.0
03 2
.975
2.9
66 2
.950
2.9
32 2
.863
2.3
38 2
.310
2.2
97 2
.285
2.2
72 2
.259
2.0
23 -
0.00
0 -
0.01
0
0.82 0.90
3.04 3.01
2.04
3.00
4.85
0.92 0.77
1.61
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j322-37-1-0325.fid2NOXDJ Mar 25 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 16PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1789.52 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -19.50 B = 26.16
Fig. S-58: 1H Spectra of compound 12b
149
.975
143
.121
131
.449
128
.360
128
.273
127
.181
127
.102
122
.821
116
.927
112
.082
77.
633
77.
200
76.
772
67.
068
62.
534
56.
795
39.
964
39.
236
37.
765
36.
167
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j322-37-1C.fidSTS-7-11C Mar 29 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 528PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6828.35 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -165.07 B = 268.88
Fig. S-59: 13C Spectra of compound 12b
S32
7.4
39
7.4
28 7
.417
7.3
61 7
.343
7.3
24 7
.320
7.2
88 7
.258
7.1
17 7
.090
7.0
64 6
.802
6.7
76 6
.651
6.6
24 4
.786
4.1
34 4
.110
4.0
94
3.0
26 3
.008
2.9
87 2
.896
2.8
72 2
.824
2.7
96 2
.790
2.3
29 2
.263
2.2
51 2
.244
2.1
55 2
.066
2.0
46
0.0
11 -
0.00
0 -
0.01
1
3.00
1.84
0.82
1.77
2.95
0.82 0.57 0.75 0.60 0.78
3.73
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j420-27-1.fidBOXD-PNO2 Jun 14 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 8PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1790.08 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -1.85 B = 52.59
Fig. S-60: 1H Spectra of compound 12c
150
.957
143
.883
136
.515
128
.655
128
.436
127
.852
127
.009
120
.787
118
.494
110
.257
77.
629
77.
200
76.
771
67.
788
58.
575
56.
054
40.
254
39.
975
37.
867
36.
443
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j420-27-1c.fidDRH-0613C Jun 16 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 400PTS1d = 16384 F1 = 75.460815 MHzF2 = 300.076874 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 7187.37 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -146.74 B = 258.21
Fig. S-61: 13C Spectra of compound 12c
S33
7.3
48
7.3
25 7
.292
7.2
84 7
.273
7.2
63 7
.256
7.2
47 7
.234
7.2
26 7
.217
7.2
06 7
.100
7.0
73 7
.048
6.6
63 6
.654
6.6
35 6
.629
4.8
54
4.1
77 4
.123
4.1
16 4
.024
3.0
30 3
.013
2.9
94 2
.910
2.7
74 2
.741
2.7
13 2
.275
2.2
66 2
.243
2.2
14 2
.100
1.2
53
-0.
000
-0.
009
3.00
1.86
1.06
2.89
1.73
0.72 0.63
11.34
0.76 1.49
10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j420-77-1.fidBOXD-PNO2 Jul 28 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 4PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1789.30 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = 0.86 B = 39.46
Fig. S-62: 1H Spectra of compound 12d
150
.161
143
.985
137
.722
136
.929
130
.962
129
.120
128
.382
127
.794
126
.876
126
.692
123
.762
121
.304
110
.645
77.
629
77.
200
76.
769
67.
927
59.
258
56.
158
40.
067
40.
011
38.
321
36.
985
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j420-77.fidSZG-27 Oct 11 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 448PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6436.69 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -152.45 B = 258.65
Fig. S-63: 13C Spectra of compound 12d
N
NS
H
H
N
NS
H
H
S34
7.3
53
7.3
44 7
.341
7.3
26 7
.305
7.2
90 7
.273
7.2
70 7
.257
7.2
48 7
.010
6.9
82 6
.296
6.2
74
4.1
40 4
.112
3.8
90 3
.866
3.8
42 3
.800
3.7
93 3
.784
3.0
75 3
.065
3.0
37 3
.022
3.0
01 2
.965
2.9
12 2
.892
2.8
53 2
.276
2.2
61 2
.249
2.2
37 2
.016
1.2
56
0.0
00
0.76 0.98
3.04
1.84
0.92
2.86
1.87
3.00
6.76
0.83
1.63
10 8 6 4 2 PPM
E:\NMR_NUTS\DATA\$j444-13-1.fidBOXD-PNO2 Aug 22 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 4PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1791.27 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -15.55 B = 61.87
Fig. S-64: 1H Spectra of compound 12e
159
.948
150
.919
143
.062
132
.123
128
.303
128
.249
127
.046
115
.322
101
.216
98.
776
77.
588
77.
176
76.
722
66.
895
62.
002
56.
401
55.
176
39.
853
39.
161
37.
354
36.
041
200 150 100 50 0 PPM
E:\NMR_NUTS\DATA\$j444-45-c1017.fidZQ-1.5 Oct 17 2011USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 304PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6824.86 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -150.04 B = 251.21
Fig. S-65: 13C Spectra of compound 12e
N
N
O
H
H
N
N
O
H
H
S35
8.
096
8.
088
8.
066
8.
057
7.
944
7.
935
7.
361
7.
355
7.
340
7.
336
7.
310
7.
303
7.
286
7.
275
7.
270
7.
259
7.
253
7.
249
7.
243
6.
634
6.
604
4.
101
4.
044
4.
024
3.
351
3.
322
3.
290
3.
273
3.
070
2.
779
2.
731
2.
713
2.
699
2.
676
2.
042
0.
000
3.00
1.74
1.04
2.71
1.61
0.71 0.66
4.56
0.79 0.76 0.73
12 10 8 6 4 2 0 PPM
E:\NMR_NUTS\data\$j420-91-3.fidBOXD-PNO2 Aug 12 2011USER: Experiment = s2pulPulse length = 10.00 usecRecycle delay = 3.00 secNA = 4PTS1d = 16384 F1 = 300.075684 MHzF2 = 75.461197 MHzSW1 = 6006.01 Hz AT1 = 2.73 secHz per Pt 1stD = 0.37 Hz O1 = 1790.91 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -11.51 B = 47.23
Fig. S-66: 1H Spectra of compound 12f
152
.319
142
.527
136
.366
128
.880
128
.346
127
.603
127
.303
125
.427
110
.037
77.495
77.074
76.648
65.353
61.821
53.807
39.449
37.535
35.315
34.881
200 150 100 50 0 PPM
E:\NMR_NUTS\data\$j444-70-c.fidwyp-24C Jan 7 2012USER: Experiment = s2pulPulse length = 7.30 usecRecycle delay = 1.00 secNA = 528PTS1d = 16384 F1 = 75.460457 MHzF2 = 300.075439 MHzSW1 = 18796.99 Hz AT1 = 0.87 secHz per Pt 1stD = 1.15 Hz O1 = 6819.53 Hz O2 = -0.50 Hz LB1 = 0.00 Hz TP A = -139.78 B = 254.15
Fig. S-67: 13C Spectra of compound 12f
N
N
O2NH
H
N
N
O2NH
H