Reactivity of N-thioamido amidines with halogenated alkyl derivatives: synthesis of 4,5-disubstituted 2-alkylaminothiazoles

2-Bromoacetate ethyl ester 4, 2-chloroacetonitrile 5, 2-bromo-1-(4-nitrophenyl)ethanone 6, and 2-chloroacetone 7 react with N-thioamido amidines 3 to yield the corresponding 4,5-disubstituted 2-alkylamino thiazoles 8, 9, 10, and 11 after the release of an amine molecule. The reaction of the amidines...

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Bibliographic Details
Published in:Journal of sulfur chemistry 2008-12, Vol.29 (6), p.593-605
Main Authors: Khilifi, Akila, Raouafi, Noureddine, Tapsoba, Issa, Boujlel, Khaled, Lamine Benkhoud, Mohamed
Format: Article
Language:English
Subjects:
4,5-disubstituted 2-alkylamino thiazoles
AM1 and PM3 semi-empirical calculations
cyclization
N-thioamido amidines
opened-ring intermediates
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Summary:2-Bromoacetate ethyl ester 4, 2-chloroacetonitrile 5, 2-bromo-1-(4-nitrophenyl)ethanone 6, and 2-chloroacetone 7 react with N-thioamido amidines 3 to yield the corresponding 4,5-disubstituted 2-alkylamino thiazoles 8, 9, 10, and 11 after the release of an amine molecule. The reaction of the amidines 3 with benzyl bromide 12, 4-chlorobutyronitrile 13, 3-bromopropionate ethyl ester 14, 3-chloropropionate ethyl ester 15, and 4-nitrobenzyl chloride 16 does not lead to the cyclic derivatives but gives opened-ring intermediates 17, 18, 19, 20, and 21. The cyclization mechanism is discussed on the basis of the study of the opened-ring intermediates which have been isolated in some cases and the AM1 and PM3 semi-empirical energetic calculations.
ISSN:1741-5993
1741-6000
DOI:10.1080/17415990802346002