Reaction of pyrimidinylacetic acid 2 with different electrophilic and nucleophilic reagents gave annulated pyrimidine derivatives 3–11, respectively. Compound 3 ([7-(dibenzothien-2-yl)-5-phenyl-2,3-dihydro-5H-thiazolo[3,2-a]-pyrimidin-6-yl]acetic acid) was transformed to pyrimidinylacetyl azide 12, which upon heterocyclisation with active methylene compounds, acidic and basic reagents furnished functionally substituted heteroaromatic compounds 13–21, respectively. The structures of the synthesised derivatives were elucidated by elemental and spectral analyses.
(a) HozA., DiazA., ElgueroJ., JimenezA., MorenoA., RuizA., and MigallonA.S., Tetrahedron2007, 63, 748; (b) S. Miwa, A. Mizokami, E.T. Keller, R. Taichman, J. Zhang and M. Namik, Cancer Res., 2005, 65, 8818.
(a) VaraprasadC.V., RamasamyK.S., GirardetJ.L., GunicE., LaiV., ZhongW., AnH., HongZ., Bioorg. Chem., 2007, 35, 25; (b) M.J. Robins, K. Miranda, V.K. Rajwanshi, M.A. Peterson, G. Andrei, R. Snoeck, E. De Clercq and J. Balzarini, J. Med. Chem., 2006, 49, 391.
4.
(a) AragonD.G., ArizaJ., VillalbaJ.M., Biochem. Pharmacol., 73, 427 (2007); (b) Z. Janeba, J. Balzarini, G. Andrei, R. Snoekc, E. De Clercq and M.J. Robins, Can. J. Chem., 2006, 84, 580.
5.
(a) NagashimaS., YokotaM., NakaiE., KuromitsuS., OhgaK., TakeuchiM., TsukamotoS., and OhtaM., Bioorg. Med. Chem., 2007, 15, 1044; (b) E.P. Falcao, S.J. De Melo, R.M. Srivastava, M.T. J. Catanho and S.C. Donascimento, Eur. J. Med. Chem., 2006, 41, 276.
6.
(a) TariL.W., HoffmanI.D., BensenD.C., HunterM.J., NixJ., NelsonK.J., Mc ReeD.E., and SwansonR.V., Bioorg. Med. Chem. Lett., 2007, 17, 688; (b) A. Gangjee, Y. Zeng, J.J. Mc Guire, R.L. Kisliuk, J. Med. Chem., 2005, 48, 5329.
7.
(a) PetricciE., MugnainiC., RadiM., TogninelliA., BernardiniC., ManettiF., ParlatoM.C., RenzulliM.L., AlongiM., FalcianiC., CorelliF., and BottaM., Arkivoc, 2006, Vii, 452; (b) I. Krizmanic, A. Visnjevac, M. Luic, L. Obrovac, M. Zinic and B. Zinic, Tetrahedron, 2003, 59, 4047.
8.
(a) GueiffierC.E., FauvelleF., DebouzyJ.C., PeinnequinA., TheryI., DabouisV., and GueiffierA., Eur. J. Pharm. Sci., 2005, 24, 219; (b) O.H. Temmink, M. De Mruin, A.W. Turksma, S. Cricca, A.C. Laan and G. J. Peters, Int. J. Biochem. Cell Biol., 2007, 39, 565.
9.
RaoJ.R., SchinaziR.F., and ChuC.K., Bioorg. Med. Chem., 2007, 15, 839.
