(<i>R</i>,<i>S</i>)-2-{[4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol

(<i>R</i>,<i>S</i>)-2-{[4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol

4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-thiol (<b>4</b>) was alkylated to 2-{[4-(4-methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenylethan-1-one (<b>5</b>) in alkaline conditions using 2-bromo-1-phenylethanone. The alkylat...

Full description

Bibliographic Details
Main Authors: Vladislav-Silvestru Valicsek, Valentin Badea
Format: Article
Language:English
Published: MDPI AG 2021-07-01
Series:Molbank
Subjects:
1,2,4-triazole-3-thiol
<i>S</i>-alkylation
secondary heterocyclic alcohol
racemic
Online Access:https://www.mdpi.com/1422-8599/2021/3/M1241
_version_ 1797518027629002752
author Vladislav-Silvestru Valicsek
Valentin Badea
author_facet Vladislav-Silvestru Valicsek
Valentin Badea
author_sort Vladislav-Silvestru Valicsek
collection DOAJ
description 4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-thiol (<b>4</b>) was alkylated to 2-{[4-(4-methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenylethan-1-one (<b>5</b>) in alkaline conditions using 2-bromo-1-phenylethanone. The alkylated compound (<b>5</b>) was reduced at the carbonyl group to the corresponding racemic secondary alcohol with an asymmetric carbon, (<i>R</i>,<i>S</i>)-2-{[4-(4-methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol (<b>6</b>). Both synthesized compounds, ketone (<b>5</b>) and secondary alcohol (<b>6</b>), are new and have not yet been reported in the literature. All the synthesized compounds were characterized by IR, 1D and 2D <sup>1</sup>H-<sup>1</sup>H, <sup>1</sup>H-<sup>13</sup>C and <sup>1</sup>H-<sup>15</sup>N NMR spectroscopy and by elemental analysis.
first_indexed 2024-03-10T07:24:26Z
format Article
id doaj.art-b16c81544daf41818676bb1bf7798479
institution Directory Open Access Journal
issn 1422-8599
language English
last_indexed 2024-03-10T07:24:26Z
publishDate 2021-07-01
publisher MDPI AG
record_format Article
series Molbank
spelling doaj.art-b16c81544daf41818676bb1bf77984792023-11-22T14:22:20ZengMDPI AGMolbank1422-85992021-07-0120213M124110.3390/M1241(<i>R</i>,<i>S</i>)-2-{[4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanolVladislav-Silvestru Valicsek0Valentin Badea1Department of Applied Chemistry and Organic and Natural Compounds Engineering, Politehnica University Timisoara, Carol Telbisz 6, RO-300001 Timisoara, RomaniaDepartment of Applied Chemistry and Organic and Natural Compounds Engineering, Politehnica University Timisoara, Carol Telbisz 6, RO-300001 Timisoara, Romania4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-thiol (<b>4</b>) was alkylated to 2-{[4-(4-methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenylethan-1-one (<b>5</b>) in alkaline conditions using 2-bromo-1-phenylethanone. The alkylated compound (<b>5</b>) was reduced at the carbonyl group to the corresponding racemic secondary alcohol with an asymmetric carbon, (<i>R</i>,<i>S</i>)-2-{[4-(4-methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol (<b>6</b>). Both synthesized compounds, ketone (<b>5</b>) and secondary alcohol (<b>6</b>), are new and have not yet been reported in the literature. All the synthesized compounds were characterized by IR, 1D and 2D <sup>1</sup>H-<sup>1</sup>H, <sup>1</sup>H-<sup>13</sup>C and <sup>1</sup>H-<sup>15</sup>N NMR spectroscopy and by elemental analysis.https://www.mdpi.com/1422-8599/2021/3/M12411,2,4-triazole-3-thiol<i>S</i>-alkylationsecondary heterocyclic alcoholracemic
spellingShingle Vladislav-Silvestru Valicsek
Valentin Badea
(<i>R</i>,<i>S</i>)-2-{[4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol
Molbank
1,2,4-triazole-3-thiol
<i>S</i>-alkylation
secondary heterocyclic alcohol
racemic
title (<i>R</i>,<i>S</i>)-2-{[4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol
title_full (<i>R</i>,<i>S</i>)-2-{[4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol
title_fullStr (<i>R</i>,<i>S</i>)-2-{[4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol
title_full_unstemmed (<i>R</i>,<i>S</i>)-2-{[4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol
title_short (<i>R</i>,<i>S</i>)-2-{[4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol
title_sort i r i i s i 2 4 4 methylphenyl 5 phenyl 4 i h i 1 2 4 triazol 3 yl thio 1 phenyl 1 ethanol
topic 1,2,4-triazole-3-thiol
<i>S</i>-alkylation
secondary heterocyclic alcohol
racemic
url https://www.mdpi.com/1422-8599/2021/3/M1241
work_keys_str_mv AT vladislavsilvestruvalicsek iriisi244methylphenyl5phenyl4ihi124triazol3ylthio1phenyl1ethanol
AT valentinbadea iriisi244methylphenyl5phenyl4ihi124triazol3ylthio1phenyl1ethanol

Similar Items