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Synthesis 1988; 1988(11): 851-854
DOI: 10.1055/s-1988-27728
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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

R. T. Chakrasali* , H. Ila, H. Junjappa
  • *Department of Chemistry, North-Eastern Hill University, Shillong 793 003, Meghalaya, India
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Publication Date:
20 August 2002 (online)

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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.