graphical contents list
TRANSCRIPT
Tetrahedron Letters Vol. 54, Issue 8, 2013
Contents
COMMUNICATIONS
Nano copper oxide mediated ligand-free C–S cross-coupling and concomitant oxidative aromatization of4-aryl-3,4-dihydropyrimidin-2(1H)-thione with diaryliodonium salts
pp 739–743
Bhagyashree Y. Bhong, Amol V. Shelke, Nandkishor N. Karade*
N
N
R1
S
R2
OI
OTf
nano CuO (10 mol %)K2CO3 (2.5 equiv)
DMF, reflux, 12 hR3R3
63-84% yield, 16 examplesR3N
H
NH
S
R1
R2
O
Penicolinates A–E from endophytic Penicillium sp. BCC16054 pp 744–748
Chakapong Intaraudom, Nattawut Boonyuen, Rapheephat Suvannakad, Pranee Rachtawee, Pattama Pittayakhajonwut*
NH3CO
O
NOR
O
n
NH3CO
O
CH3
R1 R2
Efficient synthesis and X-ray structures of new a-quinolin-3-yl-a-aminonitriles and derivatives pp 749–752
Souheila Ladraa, Fabienne Berrée, Abdelmalek Bouraiou, Sofiane Bouacida, Thierry Roisnel, Bertrand Carboni, Ali Belfaitah*
N Cl
CHO
R NH
ORNH3 Cl
COOCH3
N ClRNHR'
CN+ -
719
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Tetrahedron Letters
journal homepage: www.elsevier .com/ locate/ tet le t
Tuning the solubility of hepta(p-benzamide)s via the monomer sequence pp 753–756
Helga Seyler, Andreas Kilbinger*
Structurally diversified products from the reactions of 2-aminobenzamides with 1,3-cyclohexanedionescatalyzed by iodine
pp 757–760
Lian Lu, Mei-Mei Zhang, Hong Jiang, Xiang-Shan Wang*
NHR1
O
NH2
RNHR1
O
NHR
1
I2, 50 oC
R3
R2
O
N
O
NR
R1
R3
R2
O
80 oC
R1 = H
NH
O
NR
R3
R2
HN
HN
O
R
R3
R2
O
O
2
3 or 6
4
5
I2, 110 oC1
2
I2, 110 oC
I2
Controlling the reaction temperature at 50 �C, 80 �C, and 110 �C, respectively, the iodine-catalyzed reaction of 2-aminobenzamides with 1,3-cyclohexanedionesgave structurally diversified products. In the latter, it gave bis-quinazolin-4(3H)-ones unexpectedly, with 1,3-cyclohexanediones ring-opening.
A simple one-pot method for the mercuric oxide mediated synthesis of piperazines via oxidative diaminationof olefins
pp 761–764
Harpreet Kour, Satya Paul*, Parvinder Pal Singh, Monika Gupta, Rajive Gupta
R
R1
R2HN
R2HNHgO. 2HBF4
NR2
R2NR1
R
An efficient ecofriendly protocol for the synthesis of novel fluoro isoxazoline and isoxazolidines using N-benzylfluoro nitrone via cycloaddition reactions
pp 765–770
Bhaskar Chakraborty*, Govinda Prasad LuitelC6H5CH2NHOH
N
O H
R1 R2
Bn
R
12
3
45RCHO
[bmim]BF4 [bmim]BF4
R = 2,6 difluro/ 2 fluoro/ 3,4 difluoro/ 4 fluoro/ 2 hydroxy/ 4 hydroxy benzene/ Ph ; Bn = C6H5CH2
R1 = Ph ; R2 = COOCH3
R1 = R2 = COOCH3
R1 = R2 = COOHR3 = Et ; Ph ; R4 = H etcR3 = R4 = Ph ; R3 = Me ; R4 = Ph etc X = Cl/Br/I
+
SN2
R3CHO / R3R4CO
CR3
R4X
H
R
C
H
N+
Bn-O
R
C
H
N Bn
Hydrolysis
+ BnNH2RCHO
R2R1
CH3
CHO
[bmim]BF4
N
O H
Bn
R
12
3
45
H3CCHOendo
1-Butyl-3-methylimidazolium based ionic liquids are found to accelerate significantly the intermolecular 1,3-dipolar cycloaddition of N-benzyl fluoro nitronesderived in situ from aldehydes and benzylhydroxylamine, with electron deficient alkynes to afford enhanced rates and improved yields of isoxazolines whilewith enals exclusively endo isoxazolidines are obtained with high selectivity. Synthetic potentiality of the novel isoxazolines and nitrones has also been testedsuccessfully.
720 Contents / Tetrahedron Letters 54 (2013) 719–737
Selective fluorescence sensor for Al3+ and Pb2+ in physiological condition by a benzene based tripodal receptor pp 771–774
Barun Kumar Datta, Chirantan Kar, Arghya Basu, Gopal Das*
Fmoc-aza-b3-Lys-OAllyl and Fmoc-aza-b3-Asp-OAllyl for on-resin head-to-tail cyclization of aza-b3-peptides pp 775–778
Shoukri Abbour, Michèle Baudy-Floc’h*
NH
NHN
HN
N
HN
NH
NNH
H2N
O
OO
OO
NH
PbfN NHPbf
BocHN
NTrtN
O
O
NBoc4 3
4
OH
O
head to tail cyclization
FmocNH
NO
OH2N
4
Fmoc-Aza-β3-Lys-OAllyl
FmocNH
NHN
4
O
O NH
NHN
HN
N
HN
NH
NNH
HN
Fmoc
O
OO
OO
NH
PbfN NHPbf
BocHN
NTrtN
O
O
NBoc4 3
4
O
O
Luminescent biscyclometalated iridium(III) complex for selective and switchable Cu2+ ion binding in aqueous media pp 779–782
Fengniu Lu, Masaki Yamamura, Tatsuya Nabeshima*
Stereochemistry of theonezolides A–C pp 783–787
Kohei Nozawa, Masashi Tsuda, Naonobu Tanaka, Takaaki Kubota, Eri Fukushi, Jun Kawabata, Jun’ichi Kobayashi*
HO
CH3
CH3
OH
O O
NH
CH3O
CH3
CH3
HO3SO
O
OH
HO
HO
OH
CH3
OH OH OH OH OH OH O
CH3
SN
H3C
NH2
16
14
10
8 41
34
3536
33
19
28
2422
44 9574 4945 55 5753
63
60
SRS
S
S
S
R
R
SS
S
R
S
R SS
S
S
S
theonezolide A (1): n = 2theonezolide B (2): n = 1theonezolide C (3): n = 3
n
O
N
Contents / Tetrahedron Letters 54 (2013) 719–737 721
One-pot synthesis of bis(amino)-1,2,4-thiadiazoles via direct SNAr pp 788–791
Howard A. Beeley, Sébastien Degorce, Craig S. Harris*, Jonathan Lecoq, Rémy Morgentin, David Perkins
SN
NCl
ClS
NN
NH
NH
R1
R2
ZnCl2
DIPEAcyclohexanol,r.t. to 80 °C
R2NH2
R1NH2
One-pot
90-120 °C
The synthesis of bis(amino)-1,2,4-thiadiazoles usually relies on a four step sequence. Herein, we communicate to our knowledge the first one-potsynthesis of bis(amino)-1,2,4-thiadiazoles via a double SNAr approach.
Synthesis of dibromoolefins via a tandem ozonolysis–dibromoolefination reaction pp 792–795
Brenna Arlyce Brown*, Jonathan G. C. Veinot
Novel calix[4]arene-based receptors with bis-squaramide moieties for colorimetric sensing of anionsvia two different interaction modes
pp 796–801
Can Jin, Man Zhang, Chao Deng, Yangfan Guan, Jun Gong, Dunru Zhu, Yi Pan, Juli Jiang*, Leyong Wang
OHOH OO
NH HN
N N
O
O O
O
NO2 O2N
OHOH OO
NH HN
NH HN
O
O O
O
Anion H-bond modeAcid-base mode
A = F-, AcO-, H2PO4-
Anion
2 [HA2]-
Reactivity of 1-aminoazetidine-2-carboxylic acid during peptide forming procedures: observation of an unusualvariant of the hydrazino turn
pp 802–805
Amandine Altmayer-Henzien, Valérie Declerck, Régis Guillot, David J. Aitken*
722 Contents / Tetrahedron Letters 54 (2013) 719–737
A Europium-based luminescent chemosensor for Zn2+ with quinoxaline as the antenna pp 806–810
Xinxiu Fang, Guiyan Zhao, Yanmeng Xiao, Jingwei Xu*, Wei Yang*
Facile conversion of chromane-6-triflate to chromane-6-alanines under palladium conditions pp 811–813
Daniel K. Miller*
OR"
MeO2C NHBoc
OR"
TfO
Benzothiazines in organic synthesis: formation of a cyclopropane via neighboring group participation pp 814–816
Zhengxin Cai, Michael Harmata*
NS O
Ph
H
H
Me
OMe
H
NS O
HMe
OMe
Me MeOMs
4 equiv. imidazoleDCM, 50 °C, overnight
91%Ph
Me
The phosphorus-Claisen condensation pp 817–820
Laurent Gavara, Fabien Gelat, Jean-Luc Montchamp*
Contents / Tetrahedron Letters 54 (2013) 719–737 723
Synthesis of 3-spiropyrrolidine-3-spirooxindoles from Baylis–Hillman adducts of chromone with azomethine ylidesvia [3+2] cycloaddition reaction
pp 821–827
Panneerselvam Yuvaraj, Boreddy S. R. Reddy*
O
O OH
NH
O
OO
N
NH
NCO
ON
NH
NC O
1a- j 2a- j major 4a- j minor 5a- j
CN R R
R1
R sarcosine (3)HOO
R1
R1
OHO
CH3CN, 8 hreflux
3-Spiropyrrolidine-oxindole unit is a privileged heterocyclic motif forming the core of a large family of alkaloid natural products with strong bioactivityprofile and interesting structural properties. A novel regioselective synthesis of functionalized 3-spiropyrrolidine-3-spirooxindoles from 4-oxo-4H-chromone derivatives was accomplished by the [3+2] cycloaddition of azomethineylides with Baylis–Hillman adducts.
Concise and protecting group-free synthesis of botryolide-E pp 828–829
D. Chandra Rao, D. Kumar Reddy, V. Shekhar, Y. Venkateswarlu*
OOAc
O
OMe O
O
HO O
O
162
A short and straightforward approach towards 6-amino and 6-aminoalkyl thiazolo[4,5-c]pyridazines pp 830–833
Alessandro Stella, Steven De Jonghe, Kenneth Segers, Piet Herdewijn*
Selectivity control by silver catalysts in the cycloisomerization of 1,6-enynes derived from propiolamides pp 834–839
Jaeyoung Koo, Hyun-Sub Park, Seunghoon Shin*
R'NR M = Ag
O
R'N
H
R
O
RT R'N
H
OR
M+
R'NR
MO
R'N
OR''
(R = CH2R'')
R'N
O
(R = Ph)
R'NR
MO
724 Contents / Tetrahedron Letters 54 (2013) 719–737
Complexation to [Ru(bpy)2]2+: the trick to functionalize 3,30-disubstituted-2,20-bipyridine pp 840–842
Pascal Guillo, Olivier Hamelin*, Jacques Pécaut, Stéphane Ménage
N
N
N
NN
NRu
OH
OH N
N
N
NN
NRu
R
R
2+ 2+
R = Br, N3, Phthalimide
A catalytic, mild and efficient protocol for the C-3 aerial hydroxylation of oxindoles pp 843–846
Benjamin R. Buckley*, Beatriz Fernández D.-R.
Intramolecular cyclization of N-propargylic b-enaminones catalyzed by silver pp 847–849
Marcos A. P. Martins*, Marcelo Rossatto, Clarissa P. Frizzo, Elisandra Scapin, Lilian Buriol, Nilo Zanatta, Helio G. Bonacorso
R2
O
N
R1
R H
AgNO3
NR
R1
O
R2
NR
MeO
R2
R1
R = PrR1 = MeR2 = CF3
+
24h, 30°C 12h, 25°C
R = Pr, Bn, Ph, 4-Me-C6H4R1 = Me, Et, PrR2 = CF3, CO2Et
80% 75-90%
1,2,3-Triazoles as leaving groups in purine chemistry: a three-step synthesis of N6-substituted-2-triazolyl-adeninenucleosides and photophysical properties thereof
pp 850–853
Armands Koval�ovs, Irina Novosjolova, Erika Bizdena, Inga Biz�ane, Lina Skardziute, Karolis Kazlauskas, Saulius Jursenas,M�aris Turks*
RN
N
N
N
N3
N3N
N
N
N
N
N
NN
NN
R
R
N
N
N
N
Nu
N NN
RSugar
1 2 3
Sugar Sugar
NuH
280 nm 400 nm
Contents / Tetrahedron Letters 54 (2013) 719–737 725
Synthesis of highly efficient pH-sensitive DNA cleaving aminomethyl N-substituted cyclic enediyne andits L-lysine conjugate
pp 854–857
Ishita Hatial, Partha S. Addy, Ananta K. Ghosh, Amit Basak*
NH2
NH3
2 CF3COO
NH2R
3 CHF3CHOONH2
CF3COO
1 2 3
Lanes 1: DNA alone, 2: at pH 7.5, 3: at pH 6.5 and 4: at pH 5.5
1 2 3 4 1 2 3 4 1 2 3 4
Compound 1 Compound 2 Compound 3
HN
O
NH3
H3N
NH2R
3 CF3COOR =
NH2
NH3
2 CF3COO
Form II Form III Form I
An addition of benzylic sp3 C–H to electron-deficient olefins pp 858–860
Hong-Ying Li, Li-Juan Xing, Tong Xu, Peng Wang, Rui-Hua Liu*, Bin Wang*
NN
EWG
EWG
NN
EWG
EWG+ 100-120 °C
DMSOR R
catalyst-freeadditive-free
Convenient synthesis of multivalent zinc(II)–dipicolylamine complexes for molecular recognition pp 861–864
Shuzhang Xiao, Serhan Turkyilmaz, Bradley D. Smith*
HN
HN
SNN
N
N
N
N
NH
NHS
N
N
N N
NN
NH N
H
S NN
N
N
N
N
HN
HN S
N
N
NN
NN
H2N NH2
NH2H2N
O
N
NN
NN
N
NCS
conjugation
Use of iodine for efficient and chemoselective glycosylation with glycosyl ortho-alkynylbenzoates as donorin presence of thioglycosides
pp 865–870
Samrat Dutta, Swarbhanu Sarkar, Shyam Ji Gupta, Asish Kumar Sen*
R2OH
I2, CH3CN
OPOOR2
O
IR1
OOPOO R1O
Chemoselectively activable inpresecne of Thioglycoside
726 Contents / Tetrahedron Letters 54 (2013) 719–737
SN2 substitution reaction of 2-C-acetoxymethyl glycals catalyzed by iodine: a novel synthesis of 2-C-N-arylamidomethylglycals
pp 871–873
J. S. Yadav, G. Narasimhulu, N. Umadevi, Y. Vikram Reddy, B. V. Subba Reddy*
O
ROOR
ROOAc
O
ROOR
RO
+5 mol% I2
NHTs
CH2Cl2, r.t.
R = benzyl or ethyl
NTs
Construction of novel steroidal isoxazolidinone derivatives under Vilsmeier–Haack conditions pp 874–877
Shamsuzzaman*, Hena Khanam, Ashraf Mashrai, Nazish Siddiqui
H
H
H
X
H
H
H
X
H
H
H
COO
HNXHO H N
OH
NH2OH.HCl/CH3COONa
C2H5OH/reflux, 4 h
DMF/POCl3
stirring at 0 C for 15 min,then at 60-65 C°
°
X X X
OAc (1) OAc (4) OAc (7) Cl (2) Cl (5) Cl (8) H (3) H (6) H (9)
An efficient, ionic liquid mediated one-pot, three component sequential synthesis of 3-benzothiazolyl-2-styrylquinazolin-4(3H)-ones
pp 878–882
Mahendra Kumar*, Kailash Sharma, Dinesh Kumar Sharma, Anand Kumar Arya
N
O
O
CH3
S
NNH2
Me
N
N
O
CH3
S
N Me
1
2a
3
CHO
OMe4a N
N
O
S
N Me
5aOMe
SFILs, 80 °C SFILs, 80 °C
An efficient and diversity oriented one-pot three component sequential synthetic method has been presented for the synthesis of 3-benzothiazolyl-2-styrylquinazolin-4(3H)-ones. The synthetic method involves the reaction of 3,1-benzoxazinone with 2-aminobenzothiazole and subsequently with aromatic aldehyde using SO3H-functionalized ionicliquids (SFILs) as solvent/catalyst.
Efficient synthesis of (R)-ochratoxin alpha, the key precursor to the mycotoxin ochratoxin A pp 883–886
Cesar Antonio Lenz, Michael Rychlik*
Cl
O
OH
OR
Cl
O
O
OR
OH
O
OO
OH
Cl
O
1) LTMP, THF-50 °C, 4h
2)
-50 °C, 1hRoute A: R = HRoute B: R = CO2H
Route A: 3 steps
Route B: 1 step
(R)-Ochratoxin α
20.7 % overall yield
15.4 % overall yield
Contents / Tetrahedron Letters 54 (2013) 719–737 727
Gelsochalotine, a novel indole ring-degraded monoterpenoid indole alkaloid from Gelsemium elegans pp 887–890
Shuang Liang*, Chun-Yong He, László F. Szabó, Yi Feng*, Xiao Lin, Yuan Wang
3 1520
167 4
6
14
17
1819
5
21
22
NO
OOMe
OH
H
H
H
N-Alkylation of tosylhydrazones via a metal-free reductive coupling procedure pp 891–895
Jin-Biao Liu, Hui Yan, Gui Lu*
Ar N
R HN
Ts
NaOMe, MeOH
50 °C, 12-48 h Ar N
RN
Ts
Ar R
2
Synthesis of 5-aryl-3H-[1,3,4]oxadiazol-2-ones from N0-(chloro-aryl-methylene)-tert-butylcarbazates usingbasic alumina as an efficient and recyclable surface under solvent-free condition
pp 896–899
Kamalesh Debnath, Sudipta Pathak, Animesh Pramanik*
Rubimycinone A, a new anthraquinone from a terrestrial Streptomyces sp. pp 900–902
Ritesh Raju, Oleksandr Gromyko, Viktor Fedorenko, Jennifer Herrmann, Andriy Luzhetskyy, Rolf Müller*
728 Contents / Tetrahedron Letters 54 (2013) 719–737
The synthesis and ambipolar charge transport properties of 1,2,3,4-tetrafluoropentacene pp 903–906
Ching-Ting Chien, Ta-Chung Chiang, Motonori Watanabe, Ting-Han Chao, Yuan Jay Chang, Yan-Duo Lin, Hung-Kai Lee,Ching-Yang Liu, Chih-Hsin Tu, Chia-Hsing Sun, Tahsin J. Chow*
F
O
- CO
120 oC F
F
F
F
F
FF
A practical method for the regeneration of Kaiser-oxime resin pp 907–908
Sebastian Lüttenberg, Frank Sondermann, Jürgen Scherkenbeck*
A red fluorescent ‘turn-on’ chemosensor for Hg2+ based on triphenylamine–triazines derivatives with aggregation-induced emission characteristics
pp 909–912
Hao Zhang, Yi Qu, Yuting Gao, Jianli Hua*, Jing Li, Bo Li
A new sensitive and selective red fluorescence ‘turn on’ chemosensor 1 for Hg2+ was developed by taking advantage of AIE feature of triphenylamine–triazines motif and the specific binding of thymine with Hg2+. Moreover, chemosensor 1 exhibited large two-photon absorption cross-section (3328 GM).
Total synthesis of (±)-cis-trikentrin B via intermolecular 6,7-indole aryne cycloaddition and Stille cross-coupling pp 913–917
Nalin Chandrasoma, Neil Brown, Allen Brassfield, Alok Nerurkar, Susana Suarez, Keith R. Buszek*
NTBS
Br
Br
Br (20 equiv)
PhMe, -78 °C to rt
72%
n-BuLi ( 2.0 equiv)
NTBS
Br
NH
Br5 steps SnBu3
Pd2(dba)3 (2.5 mol%)
AsPh3 (10 mol%), THFMW, 150 °C, 23 min
73%
NH
(±)-cis-Trikentrin B
Contents / Tetrahedron Letters 54 (2013) 719–737 729
Comparison and systematic optimization of synthetic protocols for DOTA–hydrazide generation pp 918–920
Felix Fuge, Marek Weiler, Jessica Gätjens, Twan Lammers, Fabian Kiessling*
Synthesis of b-hydroxy-d-trichloromethyl-d-valerolactones by intramolecular samarium/ytterbiumdiiodide-mediated Reformatsky reaction
pp 921–924
Thies M. Schulze, Jörg Grunenberg, Stefan Schulz*
OHCl3C
OCl3C
O
Br
kinetic resolution
OO
Cl3C OHmain diastereomer
OCl3C O
O
Br
RacemateReformatsky
SmI2/YbI2
favoured
Schwartz reagent mediated synthesis of thiazolones and imidazolones from thiazolidine-2,4-diones andimidazolidine-2,4-diones
pp 925–928
Srinivasa Reddy Dandepally, Radouane Elgoummadi, Alfred L. Williams*
NR
XO
O
X = S, NH, NR
NR
XO
Cp2Zr(H)Cl
THF, rt, 1 h
12 examples
A novel reduction/elimination method of thiazolidine-2,4-dione and imidazolidine-2,4-dione derivatives using Schwartz reagent to synthesize numerousthiazolones and imidazolones in a single step is reported.
A convenient procedure for N-formylation of amines pp 929–931
Sony Joseph, Prasenjit Das, Bindu Srivastava, Hashim Nizar*, Mohan Prasad
Formamide,NaOMe YOCNHCHO
R1THF
NHR
1
R2
Formamide,NaOMeN CHO
R1
R2
R2
OOCNH2
R1
R1= Alkyl, Aryl
R2= H, Alkyl
Y= OH, NH2
730 Contents / Tetrahedron Letters 54 (2013) 719–737
Diastereoselective formation of b-hydroxyketones by the reduction of Ketene dimers pp 932–935
Pei-Hsun Wei, Melanie A. Gary, Divya Nalla, Gero D. Harzmann, Ahmad A. Ibrahim, Kyle R. Dayak, Nessan J. Kerrigan*
OO
R1
R2R2
R1
OH OR1
R2R1 R2
Reducing Agent
dr up to >99:1yield 62->99%
A general method for the diastereoselective formation of b-hydroxyketones by the reduction of ketene dimers was developed. Methylphenylketene dimerwas reduced with optimal diastereoselectivity (dr up to 6:1) using LiBH4. However, more generally LiAlH4 was found to be the most effective reducingsystem with respect to diastereoselectivity (dr up to >99:1) and yield (62–>99% for 10 examples).
The use of aqueous potassium dichloroiodate for the synthesis of ureas pp 936–940
Gil Mendes Viana, Lúcia Cruz de Sequeira Aguiar*, Jonas de Araújo Ferrão, Alessandro Bolis Costa Simas,Marcela Guariento Vasconcelos
NH
S
NHR1
NH
S
NHR1
or
NH
O
NHR1 KICl2 aq.CH3CN
or
NH
O
NHR1
NH
O
NHR1
I
method A method B(rt, 30 min) (reflux,1.5 h)
73-99%
KICl2 aq.CH3CN
77-99%
Synthesis of m-carboranyl amides via palladium-catalyzed carbonylation pp 941–944
Kiran Babu Gona, Vanessa Gómez-Vallejo, Jordi Llop*
NR1
O
R2
I
+
Pd catalystLigand
BaseCO, Pressure
NR2 R1
H
One-pot one-step reaction for the synthesis of secondary and tertiary m-carboranyl amides via palladium catalyzed carbonylation.
Biocatalytic asymmetric aldol reaction in buffer solution pp 945–948
Zong-Bo Xie, Na Wang*, Guo-Fang Jiang, Xiao-Qi Yu*
R1 H
O+ R3
R2
O
Acid buffer, 30oC R1
OH
R3
R2
OLipase
17 examples
Contents / Tetrahedron Letters 54 (2013) 719–737 731
Efficient synthesis of bulky 4-substituted-isatins via microwave-promoted Suzuki cross-coupling reaction pp 949–955
Yu-Chao Liu, Chen-Jin Ye, Qiong Chen*, Guang-Fu Yang*
NH
O
O
I
+NH
O
O
R'Pd(PPh3)4 (5 mol%)
1. R = H2. R = CH3
3
NaHCO3 (2eq)DME/H2O = 5:1 (v/v)MW(130°C), 4~12min
ArB(OH)2
R = CH3, HR' = Ar, alkenyl
R Ror
alkenyl boronic acids
39 examplesYields : 45%~95%
Mechanistic aspect of ring transformations in the reaction of 5-nitro-4-pyrimidinone with acetophenonederivatives and cycloalkanones depending on the electron density/ring size of the ketone
pp 956–959
Nagatoshi Nishiwaki*, Ryuichi Sugimoto, Kazuhiko Saigo, Kazuya Kobiro
N
NO2N
MeO
NH4OAc
N
N
NH
NO2
O
+ (CH2)n(CH2)nO
(CH2)n
NH4OAc
n = 5 n = 4, 6
Site-selective mono-oxidative addition of active zinc into carbon–bromine bond of dibrominated-thiophenes:preparation of thienylzinc reagents and their applications
pp 960–964
Hye-Soo Jung, Hyun-Hee Cho, Seung-Hoi Kim*
S BrZn*
THF
rtS ZnBr
E+
S E'+
X X X
X: 3-Br, 5-Br
Condensation of propargylic alcohols with N-methylcarbazole and carbazole in [bmim]PF6 ionic liquid; synthesis ofnovel dipropargylic carbazoles using TfOH or Bi(NO3)3Æ5H2O as catalyst
pp 965–969
G. G. K. S. Narayana Kumar, Kenneth K. Laali*
10 mol% TfOHR1
OH
R2
R = MeR1, R3= ArylR2 = PhR4 = Ph, C4H9
(bmim)PF6
N
R1
R2
R1
R2
r.t.4-6 h
65-93%
N+
R
R
20 mol% Bi(NO3)3.5H2O(bmim)PF6
70 oC16-20 h49-66%
N
R3
R4
R1
R2
R
R3
OH
R4
R = H, MeR1 = ArylR2 = Ph, C4H9
732 Contents / Tetrahedron Letters 54 (2013) 719–737
Terminal functionalization of atactic polypropylene: a new soluble polymer support pp 970–974
Binhong Lin, Devin Lawler, Gregory P. McGovern, Christopher A. Bradley, Christopher E. Hobbs*
An efficient transformation of ethers to N,N0-disubstituted ureas in a Ritter type reaction pp 975–979
Veladi Panduranga, Basavaprabhu, Vommina V. Sureshbabu*
NHCN
HN
HN
OR3
R1
R2R1
R2
R3
+BF3.Et2O (30 mol%)
AcOH, 40-50 oCO
O
HN
HN
OR3
R1
R2
HN
HN
OR3
R1
R2
O
RR
R
Enantioselective total synthesis of ())-ericanone pp 980–982
Luiz C. Dias*, Paula K. Kuroishi, Ellen C. Polo, Emílio C. de Lucca Jr.
O
HO OH
OH OH
rel-(3R,7R)-1structure proposedby Chulia's group
O
HO OH
OH OH
(3S,7S)-1structure assigned
in this work
3 73 7
Iron(III) tosylate catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via the Biginelli reaction pp 983–985
Jacob T. Starcevich, Thomas J. Laughlin, Ram S. Mohan*
Contents / Tetrahedron Letters 54 (2013) 719–737 733
A facile synthesis of annulated azolo[c][1,2,4]thiadiazine S,S-dioxides pp 986–988
Artem Cherepakha*, Vladimir O. Kovtunenko, Andrey Tolmachev
R
Hal
S
O
Cl
X YN
HNH2N
+
N
NHS
N Y
X
R
OO
Hal = F or Br X,Y = CH,CR or N
O
Bioactive cembranoids from the Red Sea soft coral Sarcophyton glaucum pp 989–992
Rania F. Abou El-Ezz, Safwat A. Ahmed, Mohamed M. Radwan, Nahla A. Ayoub, Manal S. Afifi, Samir A. Ross,Pawel T. Szymanski, Hesham Fahmy, Sherief I. Khalifa*
OO
2
HO
O
HO
3
HO
6
1
4
6
8
11
12
15
20
18
16
HO
A ring-closing metathesis approach to heterocycle-fused azepines pp 993–997
Thomas A. Moss*
NR
Het HetN
R
Grubbs (II) 5 mol%CH2Cl2 or toluene
n n
20 examples5- and 6-memberedheterocyclesRT-70 oC
The pipecolic linker—an acid-labile handle for derivatization of secondary amines on a solid-support. Part 3 pp 998–1002
Paweł Zajdel*, Nicolas Masurier, Vittorio Canale, Pascal Verdie, Muriel Amblard, Maciej Pawłowski, Jean Martinez, Gilles Subra
734 Contents / Tetrahedron Letters 54 (2013) 719–737
Graphite catalyzed green synthesis of quinoxalines pp 1003–1007
Hari K. Kadam, Salman Khan, Rupesh A. Kunkalkar, Santosh G. Tilve*
C
C
O
O
R1
R1
+NH2
NH2
R2 C
C
N
N
R1
R1
R2
GRAPHITE
Ethanol, r.t.
16 examples71 - 93 % isolated yield
Synthesis of substituted isatins pp 1008–1011
Larry L. Klein*, Michael D. Tufano
NH2
R2
R1
R2
R1
NH
O
O
NH
R2
R1
O
NOBn
isatins
H+HO2C NOBn
EDAC, HOBt
Isatins are valuable intermediates for heterocyclic chemistry. Most of the common methods for their production are less than adequate when the numberand lipophilicity of substituents on the targeted isatin are increased. Our group desired such molecules and identified an alternative method for theirproduction.
Total syntheses of (±)-folicanthine and (±)-chimonanthine via a double intramolecularcarbamoylketene–alkene [2+2] cycloaddition
pp 1012–1014
Takaaki Araki, Yuki Manabe, Kosuke Fujioka, Hiromasa Yokoe, Makoto Kanematsu, Masahiro Yoshida, Kozo Shishido*
Specific naked eye sensing of cyanide by chromogenic host: studies on the effect of solvents pp 1015–1019
Jongmin Kang*, Eun Joo Song, Hyun Kim, Young-Hee Kim, Youngmee Kim, Sung-Jin Kim, Cheal Kim*
NO2
NH
S
NN
NHost F- Cl- Br- I- CH3COO- CN- H2PO4
-
Contents / Tetrahedron Letters 54 (2013) 719–737 735
trans-3-Hydroxy-4-morpholinopiperidine—the pH-triggered conformational switch with a double flip pp 1020–1024
Andrey V. Samoshin, Hyun Joo, Andrei Ya Korneichuk, Ivan S. Veselov, Galina V. Grishina, Vyacheslav V. Samoshin*
HN
OH -H+
H+
NOH
H
H
+N
N
-H+
H+ N
O
H N
H
H
++
H
δ-
δ-δ-
O O
O
Mono- and trifluorination of the thiazole ring of 2,5-diarylthiazoles using N-fluorobenzenesulfonimide (NFSI) pp 1025–1028
Julie M. Hatfield, Cheryl K. Eidell, Chad E. Stephens*
S
N
S
N
F
F
FNFSI (3 eq)
37%(no solvent)
S
N
F
NFSI (1 eq)Bromobenzene
155 °C135-140 °C
21%
A hydrozirconation/iodination-mediated access to tetrahydroquinolizinium salts. Application to the synthesis ofLupinine and ())-Epiquinamide
pp 1029–1031
Majdi Hajri, Clément Blondelle, Agathe Martinez, Jean-Luc Vasse*, Jan Szymoniak
N+
RI-
Cp2Zr(H)Cl
then I2
N
NAc
HH
N
R
N
OHH
(-)-Epiquinamide(±)-Lupinine
OTHER CONTENTS
Corrigendum to "Application of iron carbonyl complexation to the selective total synthesis of sanshools" [TetrahedronLett. 53 (2012) 6000-6003]
p 1032
736 Contents / Tetrahedron Letters 54 (2013) 719–737
Corrigendum to ‘Synthesis of trifluoromethylated acetylenes via copper-catalyzed trifluoromethylation ofalkynyltrifluoroborates’ [Tetrahedron Lett. 53 (2012) 6646-6649]
p 1033
*Corresponding authorSupplementary data available via SciVerse ScienceDirect
Abstracted/indexed in: AGRICOLA, Beilstein, BIOSIS Previews, CAB Abstracts, Chemical Abstracts, Chemical Engineering andBiotechnology Abstracts, Current Biotechnology Abstracts, Current Contents: Life Sciences, Current Contents: Physical,Chemical and Earth Sciences, Current Contents Search, Derwent Drug File, Ei Compendex, EMBASE/Excerpta Medica, Medline,PASCAL, Research Alert, Science Citation Index, SciSearch. Also covered in the abstract and citation database SciVerse Scopus�.Full text available on SciVerse ScienceDirect�
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ISSN 0040-4039
Contents / Tetrahedron Letters 54 (2013) 719–737 737