A NEW SYNTHETIC APPROACH TO AZULENO[2,1-b]PYRIDIN-4(1H)-ONES

被引：17

作者：

Wang, Dao-Lin ^{[1
]}

Cui, Qing-Tao ^{[1
]}

Feng, Shan-Shan ^{[1
]}

Yu, Jia-Yi ^{[1
]}

机构：

[1] Bohai Univ, Liaoning Key Lab Synth & Applicat Funct Compound, Coll Chem & Chem Engn, Jinzhou 121001, Peoples R China

来源：

HETEROCYCLES | 2012年 / 85卷 / 03期

关键词：

Azuleno[2,1-b]pyridin-4(1H)-one; 1-Cyanoacetyl-2-methoxyazulene-3-carboxylate; DMFDMA; Addition-Elimination-SNAr Reaction; FACILE SYNTHESIS; DERIVATIVES;

D O I：

10.3987/COM-12-12422

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-(Dimethylamino)-2-(2-methoxy-1-ethoxycarbonylazulen-3-oyl)-acrylonitrile (4) as new synthons directed to heterocycle-fused azulene was obtained by the condensation of ethyl 1-cyanoacetyl-2-methoxyazulene-3-carboxylate (3) and N,N-dimethylformamide dimethyl acetal (DMFDMA). Reaction of this beta-enaminone with primary amines (5) in EtOH at fluxing then affords N-substituted 3-cyano-10-ethoxycarbonylazuleno[2,1-b]-pyridin-4(1H)-one derivatives (6) in good yields by a tandem addition-elimination-SNAr reaction. This reaction provides a new procedure for synthesis of pyridinone-fused azulenes.

引用

收藏

页码：697 / 704

页数：8

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