One-pot synthesis of quinazolin-4(3H)-ones and fused quinazolinones by a palladium-catalyzed domino process

被引：27
作者：
Ren, Zhi-Lin [1 ]
Kong, Han-Han [1 ]
Lu, Wen-Ting [1 ]
Sun, Mei [1 ]
Ding, Ming-Wu [1 ]
机构：
[1] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
来源：
TETRAHEDRON | 2018年 / 74卷 / 01期
基金：
中国国家自然科学基金;
关键词：
Domino reaction; Quinazolinone; Isocyanide; Carbodiimide; Palladium catalysis; AZA-WITTIG REACTION; C-H AMIDATION; ANTITUMOR EVALUATION; EFFICIENT SYNTHESIS; DERIVATIVES; ISOCYANIDE; CARBODIIMIDES; HETEROCYCLES; ACTIVATION; VASICINONE;
D O I：
10.1016/j.tet.2017.11.060
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient one-pot synthesis of quinazolin-4(3H)-ones, benzoimidazo[2,1-b]quinazolin-12(6H)-ones and imidazo[2,1-b]quinazolin-5(1H)-ones via a palladium-catalyzed domino process has been developed. The Pd-catalyzed reactions of 2-azidobenzamides 1 with isocyanides 2 produced quinazolin-4(3H)ones 4 at room temperature by a domino Pd-catalyzed cross-coupling/carbodiimide-mediated cyclization. However, as 2-azido-N-(2-bromophenyl)benzamides 1 were used under heating condition in the presence of Cs2CO3, the benzoimidazo[2,1-b]quinazolin-12(6H)-ones 5 were directly obtained by twice Pd-catalyzed domino cyclization. A domino reogioselective 5-exo-dig intramolecular cyclization reaction of alkynyl-containing azides 6 with isocyanides 2 generated imidazo[2,1-b]quinazolin-5(1H)-ones 9 in 74 -93% yields in the presence of catalyst Pd(PPh3)(4) and K2CO3. (C) 2017 Elsevier Ltd. All rights reserved.
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页码：184 / 193
页数：10
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