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

页码：7502 / 7511

页数：10

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