Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a simple approach towards N-aryl-formylpyrroles and 1,3-diaryl-formylpyrroles

摘要

A simple methodology for the conversion of substituted N-aryl-γ-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-γ-lactam 2/3-carboxylic acids were reduced to substituted (N-aryl-pyrroliden-2/3-yl)-methanols in good yields by using the NaBH4–I2 system. Aromatisation and in situ oxidation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles, which act as key starting material and intermediates in the synthesis of several bioactive compounds.