TITLE:
Dimethylformamide Dimethyl Acetal (DMFDMA) in Heterocyclic Synthesis: Synthesis of Polysubstituted Pyridines, Pyrimidines, Pyridazine and Their Fused Derivatives
AUTHORS:
Fathi A. Abu-Shanab, Sayed A. S. Mousa, E. A. Eshak, Ahmed Z. Sayed, Ahmed Al-Harrasi
KEYWORDS:
DMFDMA, Malononitrile Dimer, Pyridazine-3, 5-carbonitrile, Pyridine-4-alkoxide
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.1 No.4,
December
27,
2011
ABSTRACT: Reaction of N,N’-dimethylformamide dimethyl acetal (DMFDMA) with malononitrile dimer 8 (1:1) mole afforded 9 while, this reaction when carried out in (2:1) mole to give amidine 11 which can be used for the preparation of pyrimidine 13, amidine 14 and pyridine 19 when reacted with 4-nitroaniline, 4-methylaniline and alkoxide respectively. Malononitrile dimer reacted with diazonium chloride to give pyridazine 21, which can be reacted with DMFDMA, AcOH/HCl and cyanoacetamide to give pyridazine 22, 23 and pyrido[4,3-c] pyridazine 24 respectively. The latter reacted with DMFDMA to afford tricyclic compound 25.