Organocatalytic Syntheses of Benzoxazoles and Benzothiazoles using Aryl Iodide and Oxone via C-H Functionalization and C-O/S Bond Formation

被引：72
|
作者：
Alla, Santhosh Kumar [1 ]
Sadhu, Pradeep [1 ]
Punniyamurthy, Tharmalingam [1 ]
机构：
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, Assam, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 16期
关键词：
INTRAMOLECULAR O-ARYLATION; IN-SITU GENERATION; CATALYZED SYNTHESIS; PARALLEL SYNTHESIS; CARBOXYLIC-ACIDS; OXIDATION; VERSATILE; 2-ARYLBENZOXAZOLES; CYCLIZATIONS; DEUTERATION;
D O I：
10.1021/jo501216h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An organocatalytic protocol for the syntheses of 2-substituted benzoxazoles and benzothiazoles is described from alkyl-/arylanilides and alkyl-/arylthioanilides using 1-iodo-4-nitrobenzene as catalyst and oxone as an inexpensive and environmentally safe terminal oxidant at room temperature in air via oxidative C-H finictionalization and C-O/S bond formation. The procedure is simple and general and provides an effective route for the construction of functionalized 2-alkyl-/arylbenzoxazoles and 2-alkyl-/arylbenzothiazoles with moderate to high yields. The synthetic and mechanistic aspects have been described.
引用
收藏
页码：7502 / 7511
页数：10
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