Synthesis of 2-(2-nitrophenyl)indoline-3-acetic acid derivatives via base-catalyzed cyclization of N-(2-nitrobenzyl)-2-aminocinnamic acid derivatives

Abstract

A protocol for the synthesis of 2-(2-nitrophenyl)indoline-3-acetic acid derivatives was developed via base-catalyzed cyclization of N-(2-nitrobenzyl)-2-aminocinnamic acid derivatives. The synthetic utility of this methodology was illustrated by the concise synthesis of dihydropaullone, a partially saturated analog of paullone. Furthermore, the indoline scaffold could be further converted to the corresponding indoles and other indole-fused heterocycles.