A fast route for the synthesis of tetrazolyl oximes by a novel multicomponent reaction between Z-chlorooximes, isocyanides and trimethylsilyl azide

Mariateresa Giustiniano, Sveva Pelliccia, Ana Belen Muñoz-Garcia, Michele Pavone, Bruno Pagano, Ubaldina Galli, Ettore Novellino, Gian Cesare Tron

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

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.

Lingua originaleInglese
pagine (da-a)3549-3553
Numero di pagine5
RivistaTetrahedron Letters
Volume58
Numero di pubblicazione36
DOI
Stato di pubblicazionePubblicato - 6 set 2017

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