A new synthetic approach to azuleno[1,2-c]thiophenes

被引：17

作者：

Imafuku, K ^{[1
]}

Wang, DL

机构：

[1] Kumamoto Univ, Fac Chem, Dept Chem, Kumamoto 8608555, Japan

[2] Kumamoto Univ, Grad Sch Sci & Technol, Kumamoto 8608555, Japan

来源：

HETEROCYCLES | 2002年 / 58卷

关键词：

1-acyl-2-bromomethylazulene; thioacetamide; cyclization; heterocycle-fused azulene; azuleno[1,2-ephiophene;

D O I：

10.3987/COM-02-S(M)39

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of methyl 3-acetyl-2-bromomethylazulene-1-carboxylates (4aa-ae) and 3-acetyl-2-bromomethylazulene-1-carbonitriles (4ba-be) were obtained by the bromination of the corresponding 1-methoxycarbonyl- and 1-cyano-substituted 3-acetyl-2-methylazulenes (2aa-ae, 2ba-be), respectively, with N-bromosuccinimide. These azulenes (4aa-ae, 4ba-be) reacted with thioacetamide to give azuleno[1,2-c]thiophenes (7aa-ae, 7ba-be) in moderate yields. This reaction provides a new procedure for synthesis of thiophene-fused azulenes.

引用

页码：405 / 419

页数：15

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