Synthesis of 3-fluoromethyl-2,1-benzisoxazoles

Abstract

A convenient synthetic method to access hitherto unknown 3 (trifluoromethyl) and 3 (dif luoromethyl) 2,1 benzisoxazoles by the reaction of sodium azide with 1 (2 halophenyl) 2,2,2 trifluoroethanones or 1 (2 halophenyl) 2,2 difluoroethanones was developed. 3 Fluorometh yl 2,1 benzisoxazoles are versatile precursors for o fluoroacetylanilines.

Synthesis of 2,1-Benzoisoxazole-Containing 1,2,3-Triazoles through Copper-Catalyzed Three-Component Domino Reactions of o-Bromoacetophenones, Aldehydes, and Sodium Azide

“…Besides acting as building blocks for the construction of 1,2,3-triazoles, aryl azides could also serve as one-nitrogen source driven by the irreversible denitrogenation to form other N -containing compounds . Among these transformations, reactions related to aryl azides have also developed by combining copper-catalyzed coupling of haloarenes and NaN 3 with denitrogenative N–X (X = N, C) bond formation reactions. − Various N -containing heterocycles were efficiently constructed by this synthesis strategy. For instance, Lee’s group described an efficient synthesis of 2 H -indazole and benzimidazoles with the in situ generated aryl azido group as an electrophile or nucleophile to form the N–N or C–N bond, respectively (Scheme ).…”