Synthesis and biological evaluation of some new Thiazolo[3,2-a][1,3,5]triazine derivatives
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- Hamama, W.S., Ismail, M.A., Shaaban, S. et al. Med Chem Res (2012) 21: 2615. doi:10.1007/s00044-011-9783-1
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2-Iminothiazolidin-4-one (1) was utilized for the synthesis of several new thiazolo[3,2-a][1,3,5]triazine derivatives. 3-Phenyl-3,4-dihydro-2H-thiazolo[3,2-a][1,3,5]triazin-6(7H)-one (2) was prepared according to Mannich procedure. Both compounds 1 and 2 reacted with aromatic aldehydes to afford arylidene derivatives 3–7. Compounds 5–7 were obtained through another two routes of preparation, first when applying Mannich reaction to compounds 3 and 4 and second by reacting compounds 2 with activated olefins 11 catalyzed by triethylamine, also, the reaction of 2 with bis arylidene 16 afforded compound 18. Compound 2 reacted with both mono and di-aromatic diazonium salts to furnish 2-aryl-azothiazolo[3,2-a]triazines 20 and 21 or bis[2-azothiazolo[3,2-a]triazine]phenylene 22, respectively. Thiocarbamoyl derivatives 25 and 26 were prepared through the reaction of active methylene and imino group in 1 with phenylisothiocyanate and carbon disulfide, respectively. Structures confirmation, geometry, and biological evaluation were applied for the newly prepared compounds.