A novel acid-catalyzed rearrangement of 2-substituted-3-(2-nitrophenyl)oxiranes for the synthesis of di- and mono-oxalamides

Abstract

A novel one-pot synthetic approach to N¹-(2-carboxyaryl)-N²-(aryl or H)oxalamides from 3-(2-nitroaryl)oxirane-2-carboxamides via the classical Meinwald rearrangement and a new rearrangement sequence has been developed. The methodology is applicable to the synthesis of N-(2-carboxyphenyl)aryloxalmonoamides from (3-(2-nitrophenyl)oxiran-2-yl)(aryl)methanones. The method is operationally simple and high yielding, thus providing a new useful formula for both anthranilic acid derivatives and oxalamides.