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Paper | Regular issue | Vol 91, No. 12, 2015, pp.2271-2284
Published online, 25th November, 2015
DOI: 10.3987/COM-15-13321
Synthesis of Some Novel Thieno[3,2-d]pyrimidine Derivatives of Pharmaceutical Interest

Hala M. Refat,* Ahmed A. Fadda, Rasha E. El-Mekawy, and Aliaa M. Sleat

*Faculty of Science, Department of Chemistry, Suez Canal University, Al-Arish, 45511, Egypt


New starting material, ethyl 6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4- tetrahydrothieno[3,2-d]pyrimidine-7-carboxylate (2) was prepared by Gewald reaction using N,N-dimethylbarbituric acid. The reaction of compound 2 with phenyl isothiocyanate yields the non-isolable intermediate 3, which gave thiocarbamoyl derivative 4 upon treatment with dilute HCl. Also compound 2 react with carbon disulfide afforded carbamodithioic acid derivative 5, followed by addition of aniline to give the same product 4. On the other hand, when compound 4 refluxed in DMF and TEA afforded the thieno[2,3-d:4,5-d']dipyrimidine derivative 6. Moreover, treatment of 3 with α-halo compounds in basic medium afforded the corresponding thiazole-2-ylidene derivatives (8a, 8b, 10), thiazolidin-2-ylidene derivative 12 and 1,3-thiazinan -2-ylidene derivative 15, respectively. Furthermore, the reaction of 2 with malononitrile and 2-cyano-3-phenylacrylamide afforded the corresponding pyrido[3',2':4,5]thieno[3,2-d]pyrimidine derivatives 16 and 17, respectively. All the newly synthesized compounds were characterized by IR, 1H-NMR, 13C-NMR, mass spectra and elemental analyses.