Synthesis of 2,3-disubstituted quinolines from in situ generated imines and its enamine tautomer under radical cation induced conditions

被引：15

作者：

Jia, Xiaodong ^{[1
]}

Peng, Fangfang

Qing, Chang

Huo, Congde

Wang, Yaxin

Wang, Xicun

机构：

[1] Minist Educ, Key Lab Ecoenvironm Related Polymer Mat, Beijing, Peoples R China

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 36期

关键词：

2,3-Disubstituted quinolines; Enamine tautomer; Radical cation; Aromatization; DIELS-ALDER REACTION; HIGHLY EFFICIENT SYNTHESIS; SUBSTITUTED QUINOLINES; MOLECULAR-IODINE; BIOLOGICAL EVALUATION; TANDEM SYNTHESIS; DOMINO REACTION; CYCLIZATION; SKRAUP; ANTAGONISTS;

D O I：

10.1016/j.tetlet.2013.07.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem cyclization/aromatization of anilines and aldehydes was achieved under catalytic radical cation salt induced conditions, producing a series of 2,3-disubstituted quinolines in good yields. In this reaction, the in situ generated imine tautomerizes to enamine, which acts as a dienophile to participate in the tandem cyclization, and further elimination of the anilino group triggers the aromatization of tetrahydroquinolines, avoiding harsh conditions. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：4950 / 4952

页数：3

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