Access to Fluoroalkylated Azoles and 2-Acylaminoketones via Fluorinated Anhydride-Mediated Cleavage of NH-1,2,3-Triazoles

Abstract

NH-1,2,3-Triazoles undergo a ring cleavage in reactions with fluorinated acid anhydrides (trifluoroacetic, difluoroacetic, chlorodifluoroacetic, and pentafluoropropionic anhydrides) by nitrogen acylation and acid-mediated triazole ring opening. Structurally diverse fluoroalkylated oxazoles were prepared from 4,5-disubstituted-1,2,3-triazoles. Efficient synthesis of 2-acylaminoketones was achieved from 4-substituted 1,2,3-triazoles. Finally, easy access to fluoroalkylated imidazoles and 1,2,4-triazines was developed by a one-pot two-step route from NH-triazoles, fluorinated anhydrides, and amines or hydrazine.

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