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

Benson M Kariuki; Bakr F Abdel-Wahab; Hanan A Mohamed; Mohamed S Bekheit; Gamal A El-Hiti

doi:10.3390/molecules27248904

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. 2022 Dec 14;27(24):8904. doi: 10.3390/molecules27248904.

Authors

Benson M Kariuki¹, Bakr F Abdel-Wahab², Hanan A Mohamed², Mohamed S Bekheit³, Gamal A El-Hiti⁴

Affiliations

¹ School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK.
² Applied Organic Chemistry Department, Chemical Industries Research Institute, National Research Centre, Dokki, Giza 12622, Egypt.
³ Department of Pesticide Chemistry, National Research Centre, Dokki, Giza 12622, Egypt.
⁴ Department of Optometry, College of Applied Medical Sciences, King Saud University, Riyadh 11433, Saudi Arabia.

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.

Keywords: 1,2,3-triazoles; 1,3-thiazoles; 2-(1,2,3-triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazoles; pyrazoline; single crystal X-ray; synthesis.

MeSH terms

Chalcones*
Ethanol
Thiazoles* / chemistry

Substances

Thiazoles
Chalcones
Ethanol

Grants and funding

G.A.E.-H. acknowledges the support received from the Researchers Supporting Project (number RSP-2021/404), King Saud University, Riyadh, Saudi Arabia.