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Paper | Regular issue | Vol 71, No. 9, 2007, pp.1907-1917
Published online, 29th May, 2007
DOI: 10.3987/COM-07-10995
Synthesis of N-Imidazolidin-2-ylidenehydrazones and Their Transformation into 5,10,11,12a-Tetrahydro-6H,9H-imidazo[2’,1’:3,4][1,2,4]triazolo[1,5-c]quinazoline-6-thiones

Anita Kornicka* and Maria Gdaniec

*Department of Chemical Technology of Drugs, Medical University of Gdansk, Al. Gen. J. Hallera 107, 80-416 Gdansk, Poland

Abstract

The reaction of 2-chloro-4,5-dihydroimidazole (1) with 2-aminoacetophenone hydrazones (2a-b) afforded 1,2,3,5-tetrahydroimidazo-[2,1-b]quinazolines (3a-b) in contrast to the analogues reaction of 1 with 2-aminobenzophenone hydrazones (4a-e), which led to the formation of corresponding N-imidazolidin-2-ylidenehydrazones (5a-e). Compounds (5a-d) were further treated with carbon disulfide to give 5,10,11,12a-tetrahydro-6H,9H-imidazo[2’,1’:3,4][1,2,4]triazolo[1,5-c]quinazoline-6-thiones (6a-d). The structures of all new compounds obtained were established by elemental analyses and spectroscopic data (IR, NMR) as well as X-ray crystallographic analyses of 5a and 6a.