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E-Journal of Chemistry
Volume 9, Issue 1, Pages 131-136
http://dx.doi.org/10.1155/2012/376935

Reductive Cleavage of 1,2-Oxazines Promoted by Zinc and Ammonium Chloride; Mild One Pot Preparation of γ-Hydroxy Ketones

P. Sunil Kumar1 and K. M. Lokanatha Rai2

1FMC (I) R&D Centre, SID, Indian Institute of Science Campus, Bangalore-12, India
2Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, Karnataka-570006, India

Received 4 June 2011; Accepted 12 August 2011

Copyright © 2012 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

A facile method for a mild single pot reductive cleavage of 1,2-oxazines to γ-hydroxy ketones was developed using zinc and aqueous ammonium chloride as the reagent in methanol. The reaction involves the reduction of N-O bond of the oxazine and the hydrolysis of the resulting 1,4-iminoalcohol.