Novel Synthesis of N-Arylpyrrole, Pyrrolo[1,2-a]quinazoline, and Pyrrolo[3,4-d]pyridazine Derivatives

Abstract

Phenacyl-malononitrile derivatives 1a,b react with dimethyl formamide dimethyl acetal (DMFDMA) in refluxing toluene to afford the enaminones 2a,b respectively. Compounds 2a and 2b react with the aromatic amines (aniline, p-toluidine, p-anisidine) in refluxing ethanol to afford the pyrroles 4a–f and with anthranilonitrile and methyl anthranilate to afford the pyrrolo[1,2-a]quinazolines 5a,b and 6a,b respectively. The pyrrole derivatives 4a–f react with hydrazine hydrate and phenyl hydrazine in refluxing ethanol to afford the pyrrolo[3,4-d] pyridazine derivatives 7a–f and 8a–f respectively.

Keywords:

• Phenacylmalononitriles
• pyrroles
• pyrrolo[3,4-d]pyridazines
• pyrrolo[1,2-a]quinazolines

ACKNOWLEDGMENTS

F. M. Abdelrazek thanks the Alexander von Humboldt Foundation (Germany) for granting short research fellowships, continuous help, and support and Professor Peter Metz, Institut für Organische Chemie, TU Dresden, for his kind hospitality.