Chakrasali, R. T. ; Ila, H. ; Junjappa, H. (1988) Cycloaddition of aroyl/acylketene S,N-acetals with tosyl azide: synthesis of novel 4-aroyl/acyl-5-amino-1h-1,2,3-triazoles and 3,4-annulated 1,2,3-triazoles Synthesis, 1988 (11). pp. 851-854. ISSN 0039-7881
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Official URL: https://www.thieme-connect.com/ejournals/abstract/...
Related URL: http://dx.doi.org/10.1055/s-1988-27728
Abstract
Cycloaddition of aroyl- and acylketene S,N-acetals 1a-l with tosyl azide 2 under alkaline conditions affords novel regiospecifically substituted 4-aroyl/acyl-1-phenyl/alkyl-5-tosylamino-1H-1,2,3-triazoles 5a-1. Some of them (5a-e, g, h) are shown to undergo facile detosylation in the presence of concentrated sulfuric acid to give the corresponding 5-aminotriazoles 6a-e, g, h in excellent yields. The reaction of cyclic S,N-acetals 8a-c with 2 in dioxane at higher temperature yields the corresponding bicyclic 3-aroyl-5,6-dihydrothiazolo[3,2-c] [1,2,3]-triazoles 10a-c in good yields.
Item Type: | Article |
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Source: | Copyright of this article belongs to Thieme Medical Publishers Inc. |
ID Code: | 15491 |
Deposited On: | 13 Nov 2010 09:02 |
Last Modified: | 03 Jun 2011 06:18 |
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