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Paper | Regular issue | Vol 51, No. 7, 1999, pp.1597-1608
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8558
Imidazoquinazolinodiones — New Results

Katarzyna Kiec-Kononowicz,* Wolfgang Holzer, and Kurt Mereiter

*Department of Chemical Technology of Drug, Collegium Medicum, Jagiellonian University, ul. Medyczna 9, 30-688 Kraków, Poland

Abstract

X-Ray crystal structure determinations and spectral analyses (NMR, MS) shed new light on the reaction of 5-(Z)-arylidene-2-methylthioimidazolin-4-one (5b) with anthranilic acid, in which apart from the expected 2-(Z)-1-arylidene-2,3,5,10-tetrahydroimidazo[2,1-b]quinazoline-3,5-dione (6b) a new condensed heterocyclic system was identified, i.e. 2-(Z)-arylidene-1,2,4,5-tetrahydroimidazo[1,2-a]quinazoline-1,5-dione (8b). Reaction of the sodium salt of the 4-chioro-substituted arylidene derivative (6a) with methyl iodide surprisingly afforded 2-[(Z)-1-(4-chlorophenyl)methylene]-3-methyl-1,2,3,5-tetrahydroimidazo[1,2-a]quinazoline-1,5-dione (15).