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

页码：7186 / 7192

页数：7

共 38 条

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[22] Synthesis of Quinazolinones, Imidazo[1,2-c]quinazolines and Imidazo[4,5-c]quinolines through Tandem Reductive Amination of Aryl Halides and Oxidative Amination of C(sp3)-H Bonds
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[26] SYNTHESIS OF 1H-IMIDAZO[4,5-C]QUINOLIN-4(5H)-ONE VIA PALLADIUM-CATALYZED CYCLIZATION OF N-(2-BROMOPHENYL)-1H-IMIDAZOLE-4-CARBOXAMIDE
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