RESEARCH ARTICLE

 

Alternative synthesis of 2,4-substituted-1,3-thiazines and 2,5-substituted-thiazole derivatives

 

 

Parvesh Singh^I; Krishna Bisetty^I; Mohinder P. Mahajan^II

^IDepartment of Chemistry, Steve Biko Campus, Durban University of Technology, P.O. Box 1334, Durban 4000, South Africa
^IIDepartment of Applied Chemistry, Guru Nanak Dev University, Amritsar 143005, Punjab, India

 

 

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ABSTRACT

An easy and convenient route for the synthesis of 2,4-substituted thiazine (3-6) and 2,5-substituted thiazole (16) derivatives from phenacetamidines and glycine methyl ester is reported. To the best of our knowledge, this is the first report in which phenacetamidines have been utilized as precursors for thiazine synthesis. The syntheses of novel cyclic fused 1,3-diazabutadienes 13 and 2-aza-1,3-butadiene 17, and iodocyclization of 17 leading to the formation of thiazole 16a are also reported. In this paper a total of twenty novel compounds are reported.

Key words: Phenacetamidines, 1,3-thiazines, thiazoles, cyclizations

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Acknowledgements

Financial support to Dr Parvesh Singh for this research work by the Council of Scientific and Industrial Research (CSIR), New Delhi, India, and the National Research Foundation, Pretoria, South Africa, is gratefully acknowledged.

 

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Received 28 January 2009
Revised 29 July 2009
Accepted 27 August 2009

 

 

* To whom correspondence should be addressed. E-mail: parveshs@dut.ac.za