Synthesis and Characterization of Novel 2-(1,2,3-Triazol-4-yl)-4,5-dihydro-1<i>H</i>-pyrazol-1-yl)thiazoles and 2-(4,5-Dihydro-1<i>H</i>-pyrazol-1-yl)-4-(1<i>H</i>-1,2,3-triazol-4-yl)thiazoles

Reactions of 1-(5-methyl)-1<i>H</i>-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 pyraz...

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Bibliographic Details
Main Authors: Benson M. Kariuki, Bakr F. Abdel-Wahab, Hanan A. Mohamed, Mohamed S. Bekheit, Gamal A. El-Hiti
Format: Article
Language:English
Published: MDPI AG 2022-12-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/27/24/8904
Description
Summary:Reactions of 1-(5-methyl)-1<i>H</i>-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-<i>N</i>-thioamides. Reactions of the synthesized pyrazolin-<i>N</i>-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-1<i>H</i>-pyrazol-1-yl)thiazoles in high yields (77–90%). Additionally, 2-(4,5-dihydro-1<i>H</i>-pyrazol-1-yl)-4-(1<i>H</i>-1,2,3-triazol-4-yl)thiazoles were obtained in high yields (84–87%) from reactions with <i>N</i>-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.
ISSN:1420-3049