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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MDPI AG
2022-12-01
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| author | Benson M. Kariuki Bakr F. Abdel-Wahab Hanan A. Mohamed Mohamed S. Bekheit Gamal A. El-Hiti |
| author_facet | Benson M. Kariuki Bakr F. Abdel-Wahab Hanan A. Mohamed Mohamed S. Bekheit Gamal A. El-Hiti |
| author_sort | Benson M. Kariuki |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-09T16:01:53Z |
| format | Article |
| id | doaj.art-07444b3ed16543dcb560d9ce82b8fb84 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T16:01:53Z |
| publishDate | 2022-12-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-07444b3ed16543dcb560d9ce82b8fb842023-11-24T16:59:26ZengMDPI AGMolecules1420-30492022-12-012724890410.3390/molecules27248904Synthesis 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)thiazolesBenson M. Kariuki0Bakr F. Abdel-Wahab1Hanan A. Mohamed2Mohamed S. Bekheit3Gamal A. El-Hiti4School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UKApplied Organic Chemistry Department, Chemical Industries Research Institute, National Research Centre, Dokki, Giza 12622, EgyptApplied Organic Chemistry Department, Chemical Industries Research Institute, National Research Centre, Dokki, Giza 12622, EgyptDepartment of Pesticide Chemistry, National Research Centre, Dokki, Giza 12622, EgyptDepartment of Optometry, College of Applied Medical Sciences, King Saud University, Riyadh 11433, Saudi ArabiaReactions 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.https://www.mdpi.com/1420-3049/27/24/89042-(1,2,3-triazol-4-yl)-4,5-dihydro-1<i>H</i>-pyrazol-1-yl)thiazoles1,2,3-triazolespyrazoline1,3-thiazolessynthesissingle crystal X-ray |
| spellingShingle | Benson M. Kariuki Bakr F. Abdel-Wahab Hanan A. Mohamed Mohamed S. Bekheit Gamal A. El-Hiti 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 Molecules 2-(1,2,3-triazol-4-yl)-4,5-dihydro-1<i>H</i>-pyrazol-1-yl)thiazoles 1,2,3-triazoles pyrazoline 1,3-thiazoles synthesis single crystal X-ray |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | 2-(1,2,3-triazol-4-yl)-4,5-dihydro-1<i>H</i>-pyrazol-1-yl)thiazoles 1,2,3-triazoles pyrazoline 1,3-thiazoles synthesis single crystal X-ray |
| url | https://www.mdpi.com/1420-3049/27/24/8904 |
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