An efficient synthesis of 1-oxo-1,2-dihydrobenzo[b][1,6]naphthyridine-4-carbonitriles

被引：11

作者：

Wang, Dao-Lin ^{[1
]}

Wu, Jian-Ying ^{[1
]}

Wu, Dan ^{[1
]}

Wang, Yong-Yang ^{[1
]}

机构：

[1] Bohai Univ, Liaoning Key Lab Synth & Applicat Funct Compound, Coll Chem & Chem Engn, Jinzhou 121003, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2014年 / 25卷 / 12期

关键词：

Benzo[b][1,6]naphthyridine; 2-Cyanomethyl-4-phenylquinoline-3-carboxylate; DMFDMA; Primary amine; CARBOXAMIDE DERIVATIVES; CYTOTOXIC ACTIVITY; AAPTAMINE; ISOAAPTAMINE; ALKALOIDS; AAPTOS;

D O I：

10.1016/j.cclet.2014.07.011

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ethyl alpha-(dimethylaminomethylene)-2-cyanomethyl-4-phenylquinoline-3-carboxylate (2) as new synthons directed to 1-oxo-1,2-dihydrobenzo[b][1,6]naphthyridine-4-carbonitriles was obtained by the condensation of ethyl 2-cyanomethyl-4-phenylquinoline-3-carboxylate (1) and N,N-dimethylformamide dimethyl acetal (DMFDMA). Reaction of this enamine with primary amines (3) in HOAc-DMF at 120 degrees C then affords 2-substituted 1-oxo-1,2-dihydrobenzo[b][1,6]naphthyridine-4-carbonitrile derivatives (4) in good yields by a tandem additioneliminationcyclization reaction. (C) 2014 Dao-Lin Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

引用

页码：1555 / 1558

页数：4

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