A novel reaction between benzothiazoles and diaroylacetylenes in the presence of Meldrum's acid: ring expansion of benzothiazoles to functionalized 1,4-benzothiazines

被引：17

作者：

Adib, Mehdi ^{[1
]}

Sheibani, Esmaeil ^{[1
]}

Zhu, Long-Guan ^{[2
]}

Bijanzadeh, Hamid Reza ^{[3
]}

机构：

[1] Univ Tehran, Univ Coll Sci, Sch Chem, Tehran, Iran

[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

[3] Tarbiat Modares Univ, Dept Chem, Tehran, Iran

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 31期

关键词：

Diaroylacetylenes; Benzothiazoles; Ring expansion; Meldrum's acid; REARRANGEMENT;

D O I：

10.1016/j.tetlet.2009.04.110

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

A novel and efficient ring expansion of benzothiazoles to functionalized 1,4-benzothiazines is described. The reactive 1:1 zwitterionic intermediates formed by addition of benzothiazoles to diaroylacetylenes were trapped with Meldrum's acid under mild reaction conditions to produce 2-[2-hydroxy-2-aryl-2H-1,4-benzothiazin-3(4H)-yliden]-1-aryl-1-ethanones in excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.

引用

收藏

页码：4420 / 4422

页数：3

相关论文

共 20 条

[1]

A new, one-pot, multi-component synthesis of imines of 3-amino-2-arylimidazo[1,2-a]pyridines, 3-amino-2-arylimidazo[1,2-a]pyrazines, and 3-amino-2-arylimidazo[1,2-a]pyrimidines [J].

Abid, Mehdi ;

Sheibani, Esmail ;

Bijanzadeh, Hamid Reza ;

Zhu, Long-Guan .

TETRAHEDRON, 2008, 64 (47) :10681-10686

[2]

Efficient highly diastereoselective synthesis of 1,8a-dihydro-7H-imidazo[2,1-b][1,3]oxazines [J].

Adib, M ;

Sheibani, E ;

Mostofi, M ;

Ghanbary, K ;

Bijanzadeh, HR .

TETRAHEDRON, 2006, 62 (14) :3435-3438

[3]

A novel and simple synthesis of 9H-Pyrimido[4,5-b]indoles under microwave irradiation and solvent-free conditions [J].

Adib, Mehdi ;

Mohammadi, Bagher ;

Bijanzadeh, Hamid Reza .

SYNLETT, 2008, (02) :177-180

[4]

Reaction between isocyanides and chalcones: an effcient solvent-free synthesis of 5-hydroxy-3,5-diaryl-1,5dihydro-2H-pyrrol-2-ones [J].

Adib, Mehdi ;

Mahdavi, Mohammad ;

Noghani, Mahsa Alizadeh ;

Bijanzadeh, Hamid Reza .

TETRAHEDRON LETTERS, 2007, 48 (45) :8056-8059

[5]

A new, one-pot, three-component synthesis of 4H-pyrido[1,2-a]-pyrimidines, 4H-pyrimido[1,2-a]pyrimidines, and 4H-pyrazino[ 1,2-a] pyrimidines [J].

Adib, Mehdi ;

Sayahi, Mohammad Hosein ;

Ziyadi, Hakimeh ;

Bijanzadeh, Hamid Reza ;

Zhu, Long-Guan .

TETRAHEDRON, 2007, 63 (45) :11135-11140

[6]

A Novel One-Pot, Three-Component Synthesis of Dialkyl 5-(Alkylamino)-1-aryl-1H-pyrazole-3,4-dicarboxylates [J].

Adib, Mehdi ;

Mohammadi, Bagher ;

Bijanzadeh, Hamid Reza .

SYNLETT, 2008, (20) :3180-3182

[7]

Aitken R.A., 2008, COMPREHENSIVE HETERO, V8, P607

[8]

SYNTHETIC STUDIES IN 1,2-DITHIOLE SERIES .3. ATTEMPTS TO CONVERT DITHIOLES INTO PYRROLODITHIOLES [J].

BROWN, RFC ;

RAE, ID .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1965, 18 (07) :1071-&

[9]

Identification and quantitation of key aroma compounds formed in Maillard-type reactions of fructose with cysteamine or isothiaproline (1,3-thiazolidine-2-carboxylic acid) [J].

Engel, W ;

Schieberle, P .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (19) :5394-5399

[10]

A CONVENIENT QUATERNIZATION REARRANGEMENT PROCEDURE FOR CONVERSION OF THIAZOLES TO MEDIUM-SIZED AND LARGE-SIZED N,S-HETEROCYCLES [J].

FEDERSEL, HJ ;

GLASARE, G ;

HOGSTROM, C ;

WIESTAL, J ;

ZINKO, B ;

ODMAN, C .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) :2597-2606