Thioxopyrimidine in heterocyclic synthesis III: Synthesis and properties of some novel heterocyclic chalcone derivatives containing a thieno[2,3-d] pyrimidine-based chromophore

Cyclization of 4-methyl-2-phenyl-6-thioxo-1,6-dihydropyrimidine-5- carbonitrile 1 with chloroacetone in dmf in the presence of excess potassium carbonate anhydrous gave the 1-(5-amino-4-methyl-2-phenylthieno[2,3-d]pyrimidin- 6-yl)ethanone 3,which can react with 2,5-dimethoxytetrahydrofuran in glacial acetic acid producing the 1-[4-methyl-2-phenyl-5-(1h-pyrrol-1-yl)thieno[2,3-d] pyrimidin-6-yl]ethanone 4. on the other hand,a series of novel 3-aryl-1-[4-methyl-2-phenyl-5-(1h-pyrrol-1-yl)-thieno[2,3-d]pyrimidin-6-yl] prop-2-en-1-one chalcone dyes 6a - n were obtained by the condensation reaction of 1-[4-methyl-2-phenyl-5(1h-pyrrol-1-yl)thieno[2,3-d]-pyrimidin-6-yl]ethanone 4 with appropriate aldehydes. the structures of chalcone dyes were characterized by ir,1h nmr,mass,elemental analysis,and uv-vis spectroscopy. the dyes were applied to polyester fibers for creating hues ranging from greenish-yellow to orange; their spectral characteristics,substituent effect in dmf solution,fastness properties,and colorimetric assessment are also discussed. © 2013 yuh wen ho and wei hua yao.