An access to 1H-cyclopenta[b]pyridine-4,5-diones via condensation of 6-nitro-1,2-o-quinone with arylamines and acetone

Abstract

A facile synthesis of derivatives of a new heterocyclic 1H-cyclopenta[b]pyridine-4,5-dione system via coupling sterically crowded 3,5-di(tert-butyl)-6-nitro-1,2-benzoquinone with arylamines and acetone was developed. The reaction mechanism involving intramolecular 1,2-shift and intermolecular transfer of tert-butyl groups of the reaction intermediates was examined on the basis of DFT/B3LYP/6–311++G(d,p) (SMD) calculations