F. M. Abdelrazek, Z. E. Kandeel, A. M. Salah
1995
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0
Influential Citations
9
Citations
Journal
Heteroatom Chemistry
Abstract
ω-Bromoacetophenone reacts with the sodium salt of ethyl cyanoacetate to afford α-cyano-β-phenyl-Δαβ-butenolide. This butenolide undergoes azo coupling with diazotized aromatic amines (ArNH2) to afford the hydrazo derivatives. These hydrazo derivatives (ArPh, 4-ClC6H4, 4-MeC6H4, 4-MeOC6H4) were transformed into the corresponding 3(2H)-pyridazinone derivatives on stirring in methanol in the presence of potassium hydroxide. These latter compounds were converted into the corresponding 3-cyano-2,5-dihydroxy-4-phenyl-N-arylpyrrole derivatives on reduction with zinc dust in refluxing acetic acid, presumably via reductive cleavage of the NN bond of the pyridazine followed by recyclization via loss of ammonia.