Catalyst-free synthesis of Novel 4-(Benzofuran-2-yl)- N -phenylthiazol-2(3 H )-imines, crystal structure elucidation, and the effect of phenyl substitution on crystal packing

Abdel-Wahab, Bakr F., Kariuki, Benson M. ORCID: https://orcid.org/0000-0002-8658-3897, Mohamed, Hanan A. and El-Hiti, Gamal A. ORCID: https://orcid.org/0000-0001-6675-3126 2023. Catalyst-free synthesis of Novel 4-(Benzofuran-2-yl)- N -phenylthiazol-2(3 H )-imines, crystal structure elucidation, and the effect of phenyl substitution on crystal packing. Crystals 13 (8) , 1239. 10.3390/cryst13081239

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Abstract

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

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Additional Information:	License information from Publisher: LICENSE 1: URL: https://creativecommons.org/licenses/by/4.0/, Type: open-access
Publisher:	MDPI
ISSN:	2073-4352
Date of First Compliant Deposit:	8 September 2023
Date of Acceptance:	9 August 2023
Last Modified:	09 Sep 2023 07:57
URI:	https://orca.cardiff.ac.uk/id/eprint/162330

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