A library of twenty variously decorated 1,5-disubstituted-(1. H-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 (1. H-tetrazol-5-yl)methanone oxime to a benzoisoxazole tetrazole is reported for the first time.
A fast route for the synthesis of tetrazolyl oximes by a novel multicomponent reaction between Z-chlorooximes, isocyanides and trimethylsilyl azide / Giustiniano, Mariateresa; Pelliccia, Sveva; MUNOZ GARCIA, ANA BELEN; Pavone, Michele; Pagano, Bruno; Galli, Ubaldina; Novellino, Ettore; Tron, Gian Cesare. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 58:36(2017), pp. 3549-3553. [10.1016/j.tetlet.2017.07.098]