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Paper | Regular issue | Vol 68, No. 4, 2006, pp.687-699
Published online, 3rd March, 2006
DOI: 10.3987/COM-06-10666
Synthesis, Structure and Transformations of 2-Iminoimidazolidines into Novel Fused Heterocyclic Ring Systems

Anita Kornicka,* Franciszek Saczewski, and Maria Gdaniec

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

Abstract

Reaction of 2-chloro-4,5-dihydroimidazole (1) with 2-aminobenzylamines (2a-d) afforded 2-[(imidazolidin-2-ylideneamino)methyl]anilines (3a-d) which upon treatment with carbon disulfide gave 2,3-dihydro-12H-imidazo[2’,1’:4,5][1,3,5]thiadiazino[2,3-b]quinazolin-5-thiones (4a-d) and 3,4-dihydro-1H-quinazolin-2-thiones (5a-c). Analogous reaction of 1 with 2-aminobenzyl alcohol (6) led to the formation of [2-(4,5-dihydro-1H-imidazol-2-ylamino)phenyl]methanol hydrochloride (7) which was transformed into 1-(4H-3,1-benzoxazin-2-yl)imidazolidin-2-thione (8).