Synthesis of Novel Heterocyclic Compounds from Coupling Agent of Silane with Natural Fibers

The main goal of our work is to prepare novel heterocyclic compounds using thienopyrimidine moiety as base linked to methylchlorosilane molecule. Thus, on reacting 2-mercapto-5,6,7,8,9,10-hexahydrocycloocta[4,5] thieno- [2,3-d]pyrimidin-4(3H)-one(1)2 with either dimethyldichlorosilane or methyl Iodide, 2-((chlorodimethylsilyl)thio)-5,6,7,8,9,10-hexahydrocycloocta[4,5] thieno[2,3-d]pyrimidin-4(3H)-one (2) or (3) were obtained respectively. Compound 2 or 3 were reacted with phosphorous oxychloride to afford 4-chloro-2-((chlorodimethyl- silyl)thio)-5,6,7,8,9,10-hexahydrocycloocta [4,5] thieno[2,3-d]pyrimidine (2’) or 2-(methylthio)-5,6,7,8,9,10-hexahydro- cycloocta[4,5]thieno[2,3-d]pyrimidin-4(3H)-one (3’) respectively. Derivative 2’ or derivative 3’ was reacted easily with hydrazine hydrate (99%) to produce 4’ and 5’ respectively. The proposed reaction pathways can be illustrated by Scheme (I), Scheme (II), Scheme (III), and Scheme (IV). The structure of all newly produced compounds are confirmed according to the correct values of microanalyses and different spectral data as 1H-NMR, Mass Spectra, IR, and X-Ray diffraction.