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
收藏
页码：7717 / 7721
页数：5
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