Pyrazole-promoted synthesis of pyrrolo[3,4-c] quinoline-1,3-diones in a novel diketene-based reaction

Abstract

We describe the first classic example of green synthesis of pyrrolo[3,4-c]quinolones scaffolds by catalyst-free unusual reaction of diketene, isatin, and primary amines in ethanol in the presence of pyrazole as a promoter for 4 h. The whole structure of the new product was confirmed by X-ray analysis. The overall transformation involves the cleavage and generation of multiple carbon-nitrogen and carbon-carbon bonds. This report represents a simple and straightforward approach for the synthesis of pyrrolo[3,4-c]quinoline-1,3-diones, which has significant advantages like readily available precursors, non-use of toxic solvent, operational simplicity, mild conditions, good atom economy, and excellent yields; therefore it provides a green and sustainable strategy for access to a range of interesting N-containing heterocyclic compounds in medicinal and organic chemistry.

Keywords: diketene; green solvent; heterocycles; multicomponent reaction; pyrazole; pyrrolo[3,4-c]quinolones.