Collect. Czech. Chem. Commun. 1981, 46, 428-435

Cyclization reactions of ketenimines with some nitrogen containing compounds

Jan Světlíka and Augustin Martvoňb

a Department of Organic Chemistry, Slovak Institute of Technology, 880 37 Bratislava
b Drug Research Institute, 801 00 Bratislava


3,4-Disubstituted, 3,4,5-trisubstituted 4H-1,2,4-triazoles and 2,3-disubstituted 4(3H)-quinazolinones were prepared in one step by cyclization reactions of ketenimines with formohydrazide, acetohydrazide, benzohydrazide, thiosemicarbazide or anthranilic acid in xylene or dimethylfomamide. Reaction of diphenylketene-N-phenylimine with aminoacetaldehyde dimethyl acetal gave an adduct at the C=C bond, which afforded 2-diphenylmethyl-1-phenylimidazole with dilute HCl. 13C-NMR spectra of triazoles Id, IIa and IIb are commented.