One-Pot Synthesis of Quinazolinones from Anthranilamides and Aldehydes via p-Toluenesulfonic Acid Catalyzed Cyclocondensation and Phenyliodine Diacetate Mediated Oxidative Dehydrogenation

被引：85

作者：

Cheng, Ran ^{[1
]}

Guo, Tianjian ^{[1
]}

Zhang-Negrerie, Daisy ^{[1
]}

Du, Yunfei ^{[1
]}

Zhao, Kang ^{[1
]}

机构：

[1] Tianjin Univ, Tianjin Key Lab Modern Drug Delivery & High Effic, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 21期

基金：

中国国家自然科学基金;

关键词：

quinazolinones; cyclocondensation; dehydrogenation; phenyliodine diacetate; one-pot synthesis; N BOND FORMATION; HYPERVALENT IODINE REAGENTS; METAL-FREE; 3-COMPONENT SYNTHESIS; ORGANIC-SYNTHESIS; C-C; DERIVATIVES; QUINAZOLIN-4(3H)-ONES; DIACETOXYLATION; CONVERSION;

D O I：

10.1055/s-0033-1338521

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of 4(3H)-quinazolinones are synthesized conveniently in one pot from 2-aminobenzamides and aldehydes, via cyclization catalyzed by p-toluenesulfonic acid followed by oxidative dehydrogenation mediated by the hypervalent iodine compound phenyliodine diacetate [PhI(OAc)(2), PIDA]. Highlights of the described method include the first synthesis of quinazolinones bearing an N-alkoxy substituent, a new application of phenyliodine diacetate as an efficient dehydrogenative oxidant, and mild reaction conditions.

引用

页码：2998 / 3006

页数：9

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