Novel Synthesis of Some New Pyridazine and Pyridazino[4,5-d]pyridazine Derivatives

Abstract

Phenacyl-malononitrile derivatives 1a and b react with dimethylformamide dimethylacetal (DMFDMA) in refluxing toluene to afford the enaminones 2a and b respectively. Compounds 2a and 2b react with the hydrazine hydrate 3a and phenyl hydrazine 3b in refluxing ethanol to afford the pyridazine derivatives 5a–d, presumably via the intermediates 4. Compounds 5a–d, react with hydrazine hydrate 3a to afford the pyridazino[4,5-d]pyridazines 6a–d respectively. The pyridazines 5a and b and the pyridazino[4,5-d] pyridazines 6a and b could be oxidized into the full aromatic systems 7a and b and 8a and b respectively. Compounds 7a and b react also with hydrazine hydrate 3a to afford 8a and b respectively.

Keywords:

• Dimethylformamide-dimethylacetal
• phenacyl-malononitrile
• pyridazine
• pyridazino[4,5-d]pyridazine

ACKNOWLEDGMENTS

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