First construction of 12H-thiochromeno[2,3-b]quinolines and 5H-benzo[7,8] thiocino-[2,3-b]quinolines via intramolecular Friedel-Crafts reaction of Morita-Baylis-Hillman adducts

被引：24
|
作者：
Zhong, Weihui [1 ]
Ma, Wang [1 ]
Liu, Yanbin [1 ]
机构：
[1] Zhejiang Univ Technol, Key Lab Pharmaceut Engn, Minist Educ, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
来源：
TETRAHEDRON | 2011年 / 67卷 / 19期
基金：
中国国家自然科学基金;
关键词：
Morita-Baylis-Hillman adduct; Friedel-Crafts reaction; Acid-promoted; 12H-thiochromeno[2,3-b]quinoline; 5H-Benzo[7,8]thiocino[2,3-b]quinoline; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; ASSISTED SYNTHESIS; DERIVATIVES; QUINOLINES; LEWIS; ROUTE; HYDROXYALKYLATION; INDOLES; ACIDS;
D O I：
10.1016/j.tet.2011.03.039
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An acid-promoted intramolecular Friedel Crafts reaction of the Morita-Baylis-Hillman adducts 3 derived from 2-arylthioquinolin-3-carbaldehydes 2 was investigated. Interestingly, promoted by sulfuric acid, the substrates with electron-donating groups on the aromatic ring gave six-membered fused-ring 12H-thiochromeno[2,3-b]quinolines 4 with good yields, while those with electron-withdrawing groups afforded eight-membered fused-ring 5H-benzo[7,8]thiocino[2,3-b]quinolines 5 in moderate yields. Using triflic acid instead of sulfuric acid, only products 4 could be obtained under the similar condition. (c) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3509 / 3518
页数：10
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