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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.

SUBMITTER: Rezvanian A

PROVIDER: S-EPMC10562593 | biostudies-literature | 2023

REPOSITORIES: biostudies-literature

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

Rezvanian Atieh A Esfandsar Zahra Z

Frontiers in chemistry 20230926

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 o ...[more]

PMID: 37822773

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