New efficient synthesis of 1H-imidazo-[4,5-c]quinolines by a sequential Van Leusen/Staudinger/aza-Wittig/carbodiimide-mediated cyclization

被引：13
|
作者：
Guan, Zhi-Rong [1 ]
Liu, Zi-Ming [1 ]
Ding, Ming-Wu [1 ]
机构：
[1] Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
来源：
TETRAHEDRON | 2018年 / 74卷 / 50期
基金：
中国国家自然科学基金;
关键词：
1H-imidazo-[4,5-c]quinoline; Van Leusen reaction; Staudinger reaction; Aza-Wittig reaction; Carbodiimide; IMIDAZO-AZEPINE DERIVATIVES; ONE-POT SYNTHESIS; RECEPTORS; 7; CYCLOADDITION; AGONISTS; TLR7;
D O I：
10.1016/j.tet.2018.10.052
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new efficient synthesis of multisubstituted 1H-imidazo-[4,5-c]quinoline derivatives via sequential van Leusen/Staudinger/aza-Wittig/carbodiimide-mediated cyclization was developed. Azides 4, obtained from Van Leusen reaction of 2-azidobenzaldehyde 1, amine 2 and TosMIC (tosylmethyl isocyanide) 3, reacted with triphenyl phosphine to produce iminophosphorane 5. A tandem aza-Wittig reaction of iminophosphorane 5 with isocyanate generated 1H-imidazo-[4,5-c]quinoline 7 through carbodiimide intermediate 6 in moderate to good yield. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7186 / 7192
页数：7
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