Bimetallic Cu-Mn-Catalyzed Synthesis of 2-Arylquinazolin-4(3H)-ones: Aqueous Ammonia as Source of a Ring Nitrogen Atom

被引：9

作者：

Sharma, Rohit ^{[1
]}

Vishwakarma, Ram A. ^{[1
]}

Bharate, Sandip B. ^{[1
]}

机构：

[1] CSIR Indian Inst Integrat Med, Div Med Chem, Acad Sci & Innovat Res AcSIR, Jammu 180001, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 31期

关键词：

Nitrogen heterocycles; Heterogeneous catalysis; Copper; Manganese; Cyclization; ONE-POT SYNTHESIS; OXIDATIVE SYNTHESIS; QUINAZOLINE DERIVATIVES; CARBONYLATIVE SYNTHESIS; O-AMINOBENZAMIDES; CASCADE REACTIONS; PRIMARY ALCOHOLS; BENZYL ALCOHOLS; N-HETEROCYCLES; BOND-CLEAVAGE;

D O I：

10.1002/ejoc.201601024

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

A new method for the synthesis of 2-arylquinazolin-4-(3H)-ones that involves a three-component coupling reaction of 2-bromobenzamide, aryl aldehydes, and aqueous ammonia has been developed. This protocol employs Cu-Mn spinel oxide as a heterogeneous catalyst and does not require the presence of a ligand or external oxidant. Key features of the reaction include a recyclable catalyst, ligand-free conditions, and a wide scope of possible substrates. The mechanism begins with the replacement of the bromine atom with NH2 from aqueous ammonia followed by imine formation, intramolecular ring cyclization (C-N bond formation), and aromatization.

引用

页码：5227 / 5233

页数：7

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