4,5-Dihydro-3-methyl-5-(4-methylphenyl)-1H-pyrazole-1-carboxamide. 2003

Viktor Kettmann, and Jan Svetlík
Faculty of Pharmacy, Comenius University, Odbojarov 10, Bratislava, Slovakia 83232. kettmann@fpharm.uniba.sk

The reaction between 4-(4-methylphenyl)but-3-en-2-one and aminoguanidine produced an unexpected product of formula C(12)H(15)N(3)O, consisting of a carboxamide moiety joined to a substituted pyrazoline ring at one of the N atoms. The pyrazoline ring adopts a flat-envelope conformation and the substituted phenyl ring is oriented almost perpendicular to the heterocycle. The carbonyl O atom has partial anionic character as a result of the transfer of pi density from the two adjacent sp(2) N atoms and is involved in an intermolecular hydrogen bond with the amide group.

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