Isoquinolin-1(2H)-ones and 1,6-naphthyridin-5(6H)-ones by an N-acylation-SNAr sequence

被引：5
|
作者：
Bunce, Richard A. [1 ]
Nammalwar, Baskar [1 ]
Gnanasekaran, Krishna Kumar [1 ]
Cain, Nicholas R. [1 ]
机构：
[1] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA
来源：
TETRAHEDRON | 2014年 / 70卷 / 04期
关键词：
Isoquinolin-1(2H)-ones; 1,6-Naphthyridin-5(6H)-ones; N-acylation-SNAr sequence; SNAr by an N-acyl-beta-enaminoester; Heteroannulation; HETEROCYCLE FORMATION; AZA-ANNULATION; TANDEM; ACID; ISOQUINOLONES;
D O I：
10.1016/j.tet.2013.12.033
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthesis of 2,3-dialkyl-4-carbomethoxyisoquinolin-1(2H)-ones and 6,7-dialky1-8-carbomethoxy1,6-naphthyridin-5(6H)-ones is reported. The process involves treatment of a beta-enaminoester with 2-fluoro-5-nitrobenzoyl chloride, 2-fluorobenzoyl chloride or 2-chloronicotinoyl chloride followed by heating in the presence of base. The conversion, which proceeds by an N-acylation-SNAr reaction sequence, affords 50-86% yields when R-1 is n-alkyl but <= 30% yields when R-1 is alpha-branched. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：838 / 844
页数：7
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