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

被引：75
|
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
收藏
页码：2998 / 3006
页数：9
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