Synthesis and cyclisation studies of (E)-2-aryl-1-methy1-3-styrylquinolin-4(1H)-ones

被引：8

作者：

Rocha, Djenisa H. A.

Pinto, Diana C. G. A. ^{[1
]}

Silva, Artur M. S.

机构：

[1] Univ Aveiro, Dept Chem, P-3810193 Aveiro, Portugal

来源：

TETRAHEDRON | 2015年 / 71卷 / 40期

关键词：

(E)-2-Aryl-1-methyl-3-styrylquinolin-4(1H)-ones; Benzo[c]acridin-7(12H)-ones; 4-Arylfuro[3,2-c]quinolones; Heck reaction; N-methylation; DESIGN; ALKALOIDS;

D O I：

10.1016/j.tet.2015.07.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of (E)-2-ary1-1-methy1-3-styrylquinolin-4(1H)-ones, through the Heck reaction of 2-ary1-3-iodo-l-methyl-quinolin-4(1H)-ones with styrene is described. 2-Ary1-3-iodo-1-methy1-2-quinolin-4(1H)-ones can be obtained efficiently in a two-step transformation, methylation followed by in situ cyclization of N-(2-acetylphenyl)benzamides into 2-aryl-1-methylquinolin-4(1H)-ones, which underwent selective 3-iodination with iodine and a catalytic amount of Can. Cyclisation studies of (E)-2-ary1-1-methy1-3-styrylquinolin-4(1H)-ones under high temperature or photoinduced electrocyclisation lead to 4-aryl-2-phenylfuro[3,2-c]quinolines and 12-methyl-5-phenylbenzo[c]acridin-7(12H)-ones. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：7717 / 7721

页数：5

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