Formal [4+2] annulation of enaminones and cyanomethyl sulfur ylide: one-pot access to polysubstituted pyridin-2(1H)-ones

被引：28

作者：

Zhang, Qian ^{[1
]}

Liu, Xu ^{[1
]}

Xin, Xiaoqing ^{[1
]}

Zhang, Rui ^{[1
]}

Liang, Yongjiu ^{[1
]}

Dong, Dewen ^{[1
]}

机构：

[1] Chinese Acad Sci, Changchun Inst Appl Chem, Changchun 130022, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 97期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTIONS; ENANTIOSELECTIVE SYNTHESIS; (20S)-CAMPTOTHECIN FAMILY; EFFICIENT SYNTHESIS; CLOSING METATHESIS; SYNTHETIC METHODS; CONCISE SYNTHESIS; BRASSARDS DIENE; DELTA-LACTAMS; ACID;

D O I：

10.1039/c4cc06665k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile and efficient one-pot synthesis of polysubstituted pyridin-2(1H)-ones from readily available enaminones and the cyanomethyl sulfonium bromide salt in the presence of cesium carbonate is developed, and a mechanism involving sequential nucleophilic vinylic substitution (SNV), intramolecular nucleophilic cyclization and dealkylation reactions is proposed.

引用

页码：15378 / 15380

页数：3

共 78 条

[1] Highly enantioselective synthesis of glycidic amides using camphor-derived sulfonium salts. Mechanism and applications in synthesis [J].

Aggarwal, VK ;

Charmant, JPH ;

Fuentes, D ;

Harvey, JN ;

Hynd, G ;

Ohara, D ;

Picoul, W ;

Robiette, R ;

Vasse, JL ;

Winn, CL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) :2105-2114

[2] Additions of stabilised and semi-stabilised sulfur ylides to tosyl protected imines: Are they under kinetic or thermodynamic control? [J].

Aggarwal, VK ;

Charmant, JPH ;

Ciampi, C ;

Hornby, JM ;

O'Brien, CJ ;

Hynd, G ;

Parsons, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (23) :3159-3166

[3] Synthesis routes towards the farnesyl protein transferase inhibitor ZARNESTRA™ [J].

Angibaud, PR ;

Venet, MG ;

Filliers, W ;

Broeckx, R ;

Ligny, YA ;

Muller, P ;

Poncelet, VS ;

End, DW .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (03) :479-486

[4]

[Anonymous], CHEM BER

[5] NUCLEOPHILIC-ADDITION TO OLEFINS - KINETICS AND MECHANISM [J].

BERNASCONI, CF .

TETRAHEDRON, 1989, 45 (13) :4017-4090

[6] Kinetics of the reactions of methoxybenzylidene Meldrum's acid with thiolate ions, alkoxide ions, OH-, and water in aqueous DMSO.: Detection and kinetic characterization of the SNV intermediate [J].

Bernasconi, CF ;

Ketner, RJ ;

Chen, X ;

Rappoport, Z .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7461-7468

[7] THE CF3CH2O- ADDUCTS OF ALPHA-NITRO-BETA-(2,2,2-TRIFLUOROETHOXY)STILBENE AND BETA-METHOXY-ALPHA-NITROSTILBENE, AND THE MEO- ADDUCT OF BETA-METHOXY-ALPHA-NITROSTILBENE - KINETICS OF COMPETITION BETWEEN PROTONATION AND ACID-CATALYZED ALKOXIDE ION DEPARTURE [J].

BERNASCONI, CF ;

SCHUCK, DF ;

KETNER, RJ ;

EVENTOVA, I ;

RAPPOPORT, Z .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (10) :2719-2725

[8] [5+1] annulation: A synthetic strategy for highly substituted phenols and cyclohexenones [J].

Bi, XH ;

Dong, DW ;

Liu, Q ;

Pan, W ;

Zhao, L ;

Li, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4578-4579

[9] Diels-Alder reactions of 5,6-dihydro-2(1H)-pyridones [J].

Casamitjana, N ;

López, V ;

Jorge, A ;

Bosch, J ;

Molins, F ;

Roig, A .

TETRAHEDRON, 2000, 56 (24) :4027-4042

[10] Enantioselective aza-Diels-Alder reaction of Brassard's diene with aldimines catalyzed by chiral N,N′-dioxide-Yb(OTf)3 complex [J].

Chen, Zhenling ;

Lin, Lili ;

Chen, Donghui ;

Li, Jiangting ;

Liu, Xiaohua ;

Feng, Xiaoming .

TETRAHEDRON LETTERS, 2010, 51 (23) :3088-3091

← 1 2 3 4 5 6 7 8 →