Catalyst-Free Synthesis of Novel 4-(Benzofuran-2-yl)-N-phenylthiazol-2(3H)-imines, Crystal Structure Elucidation, and the Effect of Phenyl Substitution on Crystal Packing

A one-pot reaction of an equimolar mixture 4-methoxyaniline, phenyl isothiocyanate, and 2-bromoacetylbenzofuran in absolute ethanol the absence any catalysts afforded 4-(benzofuran-2-yl)-3-(4-methoxyphenyl)-N-phenylthiazol-2(3H)-imine with 83% yield. Under similar conditions, 4-flouroaniline provided a expected 4-(benzofuran-2-yl)-3-(4-fluorophenyl)-N-phenylthiazol-2(3H)-imine unexpected 4-(benzofuran-2-yl)-N-(4-fluorophenyl)-3-phenylthiazol-2(3H)-imine at overall 73% The structures synthesized heterocycles were confirmed using NMR spectroscopy. products recrystallized from dimethylformamide to afford samples suitable for structural determination via single-crystal diffraction. molecules share common backbone have conformations. They also display some intermolecular interactions, including C–H···X (X = N, O, π) π···π contacts. differ due methoxy fluoro substituents on their rings, resulting variations extended network crystals. Electron density maps Hirshfeld surfaces been used rationalize