intramolecular cycloaddition of azomethine ylides ... 10.1007/s10593-016-1912...chemistry of...

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  • Chemistry of Heterocyclic Compounds 2016, 52(7), 484492

    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; -mail: jbxiang@jlu.edu.cn

    1 Voronezh State University,

    1 Universitetskaya Sq., Voronezh 394006, Russia; e-mail: chocd261@chem.vsu.ru 2 People's Friendship University of Russia,

    6 Miklukho-Maklaya St., Moscow 117198, Russia; e-mail: fzubkov@sci.pfu.edu.ru

  • S2

    Spectra

    8.9

    41 8

    .847

    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

    -0.0

    00

    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

    -0.0

    00 -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

    .000

    -0.0

    11

    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

    .267

    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

    -0.0

    00

    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

    .381

    8.3

    69 8

    .365

    8.3

    56 7

    .460

    7.4

    53 7

    .443

    7.4

    36 7

    .423

    7.2

    60

    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

    .000

    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.

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