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On the chemistry of cinnoline III: Condensation reactions of (4-amino-cinnolin-3-yl)-phenyl-methanone and 4-amino-3-cinnoline-carbonitrile
Faculty
Science
Year:
2000
Type of Publication:
Article
Pages:
681-686
Authors:
AMER, AM, Asker, S, Attia, IAG, El-Mobayad, M
Journal:
POLISH JOURNAL OF CHEMISTRY POLISH CHEMICAL SOCIETY
Volume:
74
Research Area:
Chemistry
ISSN
ISI:000087029300009
Keywords :
cycloadditions, aminonitrile, cinnoline, pyridine, pyrimidine
Abstract:
(4-Amino-cinnolin-3-yl)-phenyl-methanone condensed with malononitrile, ethyl cyanoacetate, acetylacetone, ethyl acetoacetate, diethyl-malonate and ethyl thioglycolate gave the pyrido{[}3,2-c]cinnoline derivatives 3a-f respectively. (4-Amino-cinnolin-3-yl)-phenyl-methanone could be annelated to the corresponding 1,2-dihydro-4-phenyl-2-oxopyrido{[}3,2-c]cinnoline via the (4-acetamido-cinnolin-3-yl)-phenyl-methanone. Treatment of 4-amino-3-cinnolinecarbonitrile 7 with formamide, formic acid, thiourea and phenyl isothiocyanate gave pyrimidino{[}5,4-c]cinnoline derivatives. 1H-Pyrazolo{[}4,3-c]cinnoline line is also described. Chemical and spectroscopic evidences for the structures of the new compounds are presented.
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