281676-93-5Relevant academic research and scientific papers
On the chemistry of cinnoline V [1]. Reactions of 4-aminocinnolines with amines
Amer, Atef M.,El-Mobayed, Mathat M.,Asker, Sherif
, p. 595 - 604 (2004)
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-cyano5,7- dimethylcinnoline with hydrazine hydrate provided 3-amino-7,9-dimethyl-1H- pyrazolo[4,3-c]cinnoline. Moreover, (4-aminocinnolin-3-yl)phenylmethanones were treated with hydrazine hydrate to give 3-phenyl-1H-pyrazolo[4,3-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. Springer-Verlag 2003.
