As a part of our research on chemical and biological properties of imidazoline derivatives [1-4], we report the synthesis of 2-(imidazolidin-2-ylideneamino)anilines 3a-d and [2-(imidazolidin-2-ylideneamino)phenyl]methanol (7). Compounds 3a-d are further subjected to the reaction with carbon disulfide in the presence of triethylamine to give 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. A similar reaction of 7 with carbon disulfide leads to the formation of 1-(4H-3,1-benzoxazin-2-yl)imidazolidin-2-thione (8). Compounds 9 and 10 are obtained by reacting 8 with acetyl chloride and benzyl bromide, respectively. Treatment of 8 with hydrazine hydrate or methyl hydrazine affords hydrazine derivative 11.

Structures of the compounds 3a-d, 4a-d, 7-11 were established by IR, NMR and MS spectroscopic data as well as X-ray analysis of 3a, 4b and 10.

The compounds 4b-d, 8-9 and 11 were submitted to the US National Cancer Institute (Bethesda) for screening against human tumour cell lines.

*This work was supported by the Polish State Committee for Scientific Research (Grant 6 PO5F 03821).

References:

1. Kornicka A., Sączewski F., Gdaniec M.: Molecules 2004, 9, 86-101.

2. Sączewski F., Kornicka A., Gdaniec M., Hałasa R., Werel W.: Eur. J. Org. Chem. 2004, 3511-3515.

3. Kornicka A., Sączewski F., Petrusewicz J., Rejdych A., Tyacke R.J., Hudson A.L., Hutt D.J.: Pol. J. Chem. 2005, 79, 89-100.

4. Kornicka A., Sączewski F., Tyacke R.J., Hudson A.L., Hutt D.J.: Acta Polon. Pharm.-Drug Res. 2005, 62, 497-502.

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