Facile synthesis of some novel pyrrole and pyridazinoquinazolone derivatives

Autor:	Ahmad M. Farag, Zaghloul E. Kandeel, Fathy M. Abdelrazek
Rok vydání:	1995
Předmět:	chemistry.chemical_classification Ammonia chemistry.chemical_compound Acetic acid Aqueous solution chemistry Derivative (finance) Reductive cleavage Moiety Aromatic amine General Chemistry Medicinal chemistry Pyrrole
Zdroj:	Heteroatom Chemistry. 6:281-285
ISSN:	1098-1071 1042-7163
DOI:	10.1002/hc.520060314
Popis:	3-Dicyanomethylene-3-phenylpropionitrile coupled with diazotized aromatic amines (Ar-NH2) to afford hydrazono derivatives. The latter (Ar = C6H5, 4-CH3C6H4, 4-CH3OC6H4, and 4-ClC6H4) were readily cyclized upon reflux in aqueous NaOH to 3(2H) pyridazinimine derivatives, which were readily transformed into their corresponding pyridazinone derivatives on reflux in ethanolic HCl. The pyridazinimines undergo reductive cleavage and recyclization via loss of ammonia to afford the corresponding N-aryl pyrroles on reflux in glacial acetic acid with Zn dust. The pyridazinone derivatives, however, undergo the same reaction but with loss of the aromatic amine moiety to afford only one pyrrolone derivative. The hydrazono derivative (Ar = 2-NCC6H4) was cyclized into pyridazino[3,2-b]quinazolin-6-imine, which is easily converted into pyridazino[3,2-b]quinazolin-6-one on reflux in ethanolic HCl. The latter compound is also obtained from the hydrazo derivatives (Ar = 2-HOOCC6H4 and 2-MeOOCC6H4) by reflux in aqueous NaOH.
Databáze:	OpenAIRE
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