A fast route for the synthesis of tetrazolyl oximes by a novel multicomponent reaction between Z-chlorooximes, isocyanides and trimethylsilyl azide. Issue 36 (6th September 2017)

• Record Type: Journal Article
• Authors: Giustiniano, Mariateresa; Pelliccia, Sveva; Muñoz-Garcia, Ana Belen; Pavone, Michele; Pagano, Bruno; Galli, Ubaldina; Novellino, Ettore; Tron, Gian Cesare
• Is Part Of: Tetrahedron letters. Volume 58:Issue 36(2017)
• Page Start: 3549
• Page End: 3553
• Publication Date: 2017-09-06
• Subjects: Multicomponent reactions -- Isocyanides -- Z-Chlorooximes -- [3+1] cycloaddition -- (1H-Tetrazol-5-yl)methanone oximes; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.07.098
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A one-pot synthesis of (1 H -tetrazol-5-yl)methanone oximes has been reported. The combination of ( Z )-chlorooximes, isocyanides and TMSN3 has been exploited. A cyclization to benzoisoxazole tetrazoles has been reported for the first time. Abstract: 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.