Cycloaddition of Sodium Azide to Polarized KeteneS,S- andS,N-Acetals: Synthesis of Novel Substituted Triazole and Tetrazole Derivatives
- 1 January 1988
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1988 (06) , 453-455
- https://doi.org/10.1055/s-1988-27604
Abstract
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.Keywords
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