Synthesis and characterization of novel 2-(1,2,3-triazol-4-yl)-4,5-dihydro-1 h -pyrazol-1-yl)thiazoles and 2-(4,5-dihydro-1 h -pyrazol-1-yl)-4-(1 h -1,2,3-triazol-4-yl)thiazoles

Kariuki, Benson M. ORCID: https://orcid.org/0000-0002-8658-3897, Abdel-Wahab, Bakr F., Mohamed, Hanan A., Bekheit, Mohamed S. and El-Hiti, Gamal A. ORCID: https://orcid.org/0000-0001-6675-3126 2022. Synthesis and characterization of novel 2-(1,2,3-triazol-4-yl)-4,5-dihydro-1 h -pyrazol-1-yl)thiazoles and 2-(4,5-dihydro-1 h -pyrazol-1-yl)-4-(1 h -1,2,3-triazol-4-yl)thiazoles. Molecules 27 (24) , 8904. 10.3390/molecules27248904

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Abstract

Reactions of 1-(5-methyl)-1H-1,2,3-triazol-4-yl)ethan-1-ones and benzaldehydes in ethanol under basic conditions gave the corresponding chalcones. Reactions of the chalcones combined with thiosemicarbazide in dry ethanol containing sodium hydroxide afforded the corresponding pyrazolin-N-thioamides. Reactions of the synthesized pyrazolin-N-thioamides and several ketones (namely, ethyl 2-chloro-3-oxobutanoate, 2-bromoacetylbenzofuran, and hydrazonoyl chloride) gave the corresponding novel 2-(1,2,3-triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazoles in high yields (77–90%). Additionally, 2-(4,5-dihydro-1H-pyrazol-1-yl)-4-(1H-1,2,3-triazol-4-yl)thiazoles were obtained in high yields (84–87%) from reactions with N-pyrazoline-thioamides and 4-bromoacetyl-1,2,3-triazoles under basic conditions. The structures of six of the newly synthesized heterocycles were confirmed by X-ray crystallography.

Item Type:	Article
Date Type:	Published Online
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
Date of First Compliant Deposit:	6 January 2023
Date of Acceptance:	12 December 2022
Last Modified:	06 May 2023 18:25
URI:	https://orca.cardiff.ac.uk/id/eprint/155464

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