Synthesis, reactions and DFT calculations of novel bis(chalcones) linked to a thienothiophene core through an oxyphenyl bridge

Abstract

A synthesis of novel isomeric bis(chalcones) based-thienothiophene and study of their synthetic utilities as building blocks for novel bis(dihydroisoxazoles), bis(dihydropyrazoles) and bis(dihydropyrimidines) each linked to a thienothiophene core through an oxyphenyl bridge is reported. Density functional theory (DFT) calculations at the B3LYP/6-31G level of theory have been carried out to investigate the equilibrium geometry of the novel isomeric chalcones 7 and 10. Moreover, total energy, energy of the HOMO and LUMO and Mullikan atomic charges were calculated. In addition, the dipole moment and orientation of the two π-isoelectronic chalcones 7 and 10 have been measured and their interactions with hydrazine hydrate to form dihydropyrazoles have been studied.