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Synfacts 2008(4): 0358-0358  
DOI: 10.1055/s-2008-1042852
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Oxidative Cyclization of ortho-Phenolic and Thiophenolic Imines

Contributor(s): Victor Snieckus, Johnathan Board
C. Praveen, K. Hemanth Kumar, D. Muralidharan, P. T. Perumal*
Central Leather Research Institute, Tamil Nadu, India
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

Reported is the oxidative synthesis of benzothiazoles and benzoxazoles from ortho-phenolic and ortho-thiophenolic imines using pyridinium chlorochromate (PCC) supported on silica. A mechanism is proposed involving acid-induced attack of the phenol or thiophenol lone pair on the imine to close the ring, followed by single-electron-transfer oxidation to yield the product.