A fast route for the synthesis of tetrazolyl oximes by a novel multicomponent reaction between Z-chlorooximes, isocyanides and trimethylsilyl azide
2017
Giustiniano, Mariateresa | Pelliccia, Sveva | Muñoz-Garcia, Ana Belen | Pavone, Michele | Pagano, Bruno | Galli, Ubaldina | Novellino, Ettore | Tron, Gian Cesare
A library of twenty variously decorated 1,5-disubstituted-(1H-tetrazol-5-yl)methanone oximes was prepared in one single synthetic step exploiting the combination of (Z)-chlorooximes, isocyanides and trimethylsilyl azide. The formal [3+1] cycloaddition between isocyanides and nitrile N-oxides with respect to the [3+1] cycloaddition between isocyanides and azides prevails, while the direct attack of azide onto nitrile N-oxides remains competitive. Finally, an intramolecular cyclization of a (1H-tetrazol-5-yl)methanone oxime to a benzoisoxazole tetrazole is reported for the first time.
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