The Research On The Synthesis Of Pyrimidine And Thiophene Derivatives

Pyrimidine and thiophene heterocyclic derivatives widespread existed in nature as biology and natural products. For their significant therapeutic properties, pharmacological and biological activities, continue research for developing new, facile and convenient procedure to synthesize pyrimidine and thiophene derivatives has never disconnected during these decades. In this thesis we initiated the synthetic study of 3,4-dihydropyrimidine-2-(1H)-ones, 4(3H)-quinazolinones, thieno[2, 3-d]pyrimidin-4 (3H)-one, thieno[2, 3-b]thiophenes. A series of significant results and developments have been achived and the main interesting results are as follows:1. Optimization research of Biginelli reaction. We have disclosed one-pot catalytic synthesis of 3,4-dihydropyrimidine-2-(1H)-ones and oxygen-bridged pyrimidine tricyclic derivatives, which proceeds in good yield under mild conditions. The single crystal structures of six products were determined by X-ray diffraction method.2. Zn(ClO4)2 catalyzed synthesis of 4(3H)-quinazolinones. Different metal perchlorates were screened to catalyze the three-component reaction of anthranilic acid, triethyl orthoformate and amines to afford 4(3H)-quinazolinones in solvent-free conditions. Zn(ClO4)2 was demonstrated to be efficient to catalyze the reaction. The procedure is mild and clear, improved yields for both anilines and primary amines make it a useful and attractive process for the synthesis of 4(3H)-quinazolinones. The structures were fully characterized by NMR, Mass, IR spectra and a single crystal structure was also confirmed by X-ray diffraction method.3. Zn(OAc)2 catalyzed synthesis of substituted thieno[2, 3-d]pyrimidin-4(3H)-one under microwave irradiation. In this work, we found Zn(OAc)2 can catalyze the cyclization of the 2-aminothiophene-3-carboxylate, triethyl orthoformate and anilines to construct thieno[2, 3-d]pyrimidin-4(3H)-ones under microwave irradiation in good yield. Moreover, six novel thieno[2, 3-b]thiophene derivatives were synthesized via one-pot procedure usingβ-dicarbonyl compounds, carbon disulfide and halomethyl derivatives. Two products of this chapter were determined by X-ray diffraction method.