S. Sanad, Ahmed E. M. Mekky
Apr 1, 2018
Citations
1
Influential Citations
16
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
2-Acetyl-5,7-dibromobenzo[b]furan (1) reacted with dimethylformamide-dimethylacetal to give the corresponding (E)-enaminone 3 which coupled with aromatic diazonium chloride to afford the corresponding key intermediates 3-oxo-2-(2-arylhydrazono)propanals 6a,b. Compounds 6a,b were used to prepare novel 3-imino-2,3-dihydropyridazines 10a,b and 6-phenylazopyrido[2,3-d]pyrimidin-4(1H)-one derivatives 15a, b through their reaction with acetonitrile derivatives 8a,b and 6-aminopyrimidin-4(1H)-one 13, respectively. On the other hand, the enaminone 3 was taken as a synthetic precursor to synthesize novel pyrazolo[5,1-c] [1,2,4]triazines 21a–c, [1,2,4]triazolo[3,4-c][1,2,4]triazines 25 and benzimidazo[2,1-c][1,2,4]triazine 29 containing 5,7-dibromobenzofuran-2-oyl moiety via its coupling with the appropriate diazonium salts of a variety of hetero-armomatic amines in a facile one-step route.