Studies On Synthesis And Properties Of Thienopyrimidinone Derivatives

Thienopyrimidinones have became to be the highlight field of agrochemistry and medicine research, after being found to show widespread biological activities. In this paper, we studied the synthesis of novel thienopyrimidine derivatives via aza-Wittig reaction. 44 unreported thienopyrimidinone derivatives in 4 series have been synthesized via thienyliminophosphorane with aliphatic isocyanates or carbon disulfide. The structure of these compounds were confirmed by ~1H NMR, IR, MS, elemental analysed and X-ray diffraction. It may be summarized as follows:Ⅰ2-alkylamino-3-alkyl-5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4(3H)-ones (6 Comp.)Ⅱ2-alkyloxyl-3-alkyl-5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4(3H)-ones (8 Comp.)Ⅲ2-aryloxyl-3-alkyl-5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4(3H)-ones (13 Comp.)Ⅳ2-alkyl(aryl)thio-5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4(3H)-ones (15 Comp.) (15个)The reaction of N-thienyl, N'-alkyl-carbodiimides with various neucleophiles such as amines, alcohols, phenols etc was studied. Our research indicated that the mixed solvent of ethanol and methylene chloride as well as the catalysis of sodium ethoxide is critical to the cyclizaton of guanidine.The selectivity of cyclization of the carbodiimide with primary amines was investigated also. There is a good selectivity of the cyclization according to the steric hindrance and electron effect of the primary amine.Finally, the primary bioassays of the new compounds mentioned above were measured.