1394240-56-2Relevant academic research and scientific papers
Condensation reactions of 3-oxo-2-arylhydrazonopropanals with active methylene reagents: Formation of 2-hydroxyand 2-amino-6-substituted-5- arylazonicotinates and pyrido[3,2-c]cinnolines via 6π-electrocyclization reactions
Al-Mousawi, Saleh M.,El-Apasery, Morsy A.
experimental part, p. 6547 - 6556 (2012/09/08)
3-Oxo-3-phenyl-2-(p-tolylhydrazono)propanal (1a) undergoes condensation with ethyl cyanoacetate in acetic acid in the presence of ammonium acetate to yield either 2-hydroxy-6-phenyl-5-p-tolylazonicotinic acid ethyl ester (6a) or 2-amino-6-phenyl-5-ptolylazonicotinic acid ethyl ester (8), depending on the reaction conditions. Similarly, other 3-oxo-3-aryl-2-arylhydrazonopropanals 1a,b condense with active methylene nitriles 2c,d to yield arylazonicotinates 6b,c. In contrast, 2-[(4-nitrophenyl)-hydrazono]-3-oxo-3-phenyl-propanal (1c) reacts with ethyl cyanoacetate to yield ethyl 6-(4-nitrophenyl)-2-oxo-2,6- dihydropyrido[3,2-c]cinnoline-3-carboxylate (11), via a novel 6π-electrocyclization pathway. Finally, 3-oxo-2-(phenylhydrazono)-3-p- tolylpropanal (1d) condenses with 2a-c to yield pyridazinones 13a-c.
