On the Chemistry of Cinnoline V [1]. Reactions of 4-Aminocinnolines with Amines |
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Authors: | Email author" target="_blank">Atef M?AmerEmail author Mathat M?El-Mobayed Sherif?Asker |
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Institution: | (1) Chemistry Department, Faculty of Science, Zagazig University, Zagazig, Egypt |
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Abstract: | Summary. We describe the effect of the solvent during the intra-cyclization of the arylhydrazonomalononitrile to obtain new and useful substituted cinnolines, namely 4-amino-3-cyanocinnolines and (4-amino-cinnolin-3-yl)arylmethanones. 4-Amino-3-cyano-5,7-dimethyl-cinnoline was treated with n-hexylamine, cyclohexylamine, and isopropylamine to yield the corresponding cinnoline-3-carboxamidine derivatives. Furthermore, 4-amino-3-cyano-5,7-dimethylcinnoline was reacted with diaminoethane to give 4-amino-5,7-dimethyl-3-(4,5-dihydroimidazol-2-yl)cinnoline. Treatment of 4-amino-3-cyano-5,7-dimethylcinnoline with hydrazine hydrate provided 3-amino-7,9-dimethyl-1H-pyrazolo4,3-c]cinnoline. Moreover, (4-aminocinnolin-3-yl)phenylmethanones were treated with hydrazine hydrate to give 3-phenyl-1H-pyrazolo4,3-c]cinnolines. Finally, reactions of (4-aminocinnolin-3-yl)phenylmethanone with 3,5-dimethylaniline, phenyl hydrazine, hydroxylamine, and phenyl isothiocyanate are discussed. Chemical and spectroscopic evidence for the structures of the new compounds is presented. |
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Keywords: | , Cycloadditions, Hydrazones, Cinnolines, Pyrazoles, Amines, |
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