Synthesis of 2,5-diphenyl-3,4-di(phenylethenyl)cyclopentadienone, -pyrrole and -thiophene

Abstract

2,5-Diphenyl-3,4-di(phenylethenyl)cyclopentadienone (2), -pyrrole (3), and -thiophene (4) have been synthesized by bi-steps strategy. Step one involves the synthesis of cinnamil (1) by the condensation of 2,3-butanedione with benzaldehyde in the presence of Pyrrolidine as a catalyst. Step two involves the synthesis of 2,5-diphenyl-3,4-di(phenylethenyl)cyclopentadienone (2), -pyrrole (3), and -thiophene (4) by the condensation of cinnamil (1) with dibenzyl ketone, dibenzylamine, and dibenzyl sulfide, respectively in the presence of sodium hydride (base) and methylene chloride (solvent) while stirring. 1HNMR, LC-MS, IR, UV-visible, and fluorescence spectroscopy were used to confirm these products (2-4). Our method facilitated the proficient installation of four various groups on the cyclopentadienone (2), pyrrole (3), and thiophene (4) rings in two steps with an extended conjugated framework.