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

Author

Pradeep Sadhu, Santhosh Kumar Alla, and Tharmalingam Punniyamurthy

Subjects
chemistry.chemical_classification, Benzoxazoles, Molecular Structure, Chemistry, Aryl, Organic Chemistry, Iodide, Oxidation reduction, Iodides, Bond formation, Catalysis, chemistry.chemical_compound, Organic chemistry, Molecule, Surface modification, Anilides, Benzothiazoles, Oxidation-Reduction, Nitrobenzenes
Abstract

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 functionalization 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.

Published
2014
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