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Synthesis 1988; 1988(6): 453-455
DOI: 10.1055/s-1988-27604
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Cycloaddition of Sodium Azide to Polarized Ketene S,S- and S,N-Acetals: Synthesis of Novel Substituted Triazole and Tetrazole Derivatives

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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Thermal [3+2] cycloadditon of aroylketene dithioacetals 1a-e with sodium azide affords novel 4-aroyl-5-methylthio-1H-1,2,3-triazoles 3a-e. The corresponding S,N-acetals 5a-m derived from primary amines react with sodium azide through different pathway involving cyclization of initially formed imidoyl azide intermediates to give novel 1,5-disubstituted tetrazole 7a-m in good yields. The S,N-acetal 5n obtained from malononitrile, however, undergoes cycloaddition on one of the nitrile groups to give a tetrazole 8.

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