Synthesis and oxidation of some azole-containing thioethers
Pyrazole and benzotriazole-containing thioethers, namely 1,5-bis(3,5-dimethylpyrazol-1-yl)-3-thiapentane, 1,8-bis(3,5-dimethylpyrazol-1-yl)-3,6-dithiaoctane and 1,3-bis(1,2,3-benzotriazol-1-yl)-2-thiapropane were prepared and fully characterized. Oxidation of the pyrazole-containing thioether by hyd...
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doaj-0b762220cde84e1aa06e96d2a3e807d32021-02-02T04:43:11ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-11-01711526153210.3762/bjoc.7.1791860-5397-7-179Synthesis and oxidation of some azole-containing thioethersAndrei S. Potapov0Nina P. Chernova1Vladimir D. Ogorodnikov2Tatiana V. Petrenko3Andrei I. Khlebnikov4Department of Chemistry, Altai State Technical University, 46 Lenin Ave., 656038 Barnaul, RussiaDepartment of Chemistry, Altai State Technical University, 46 Lenin Ave., 656038 Barnaul, RussiaInstitute of Petroleum Chemistry, Siberian Branch of the Russian Academy of Sciences, 3 Akademicheskii Ave., 634055 Tomsk, RussiaInstitute of Petroleum Chemistry, Siberian Branch of the Russian Academy of Sciences, 3 Akademicheskii Ave., 634055 Tomsk, RussiaDepartment of Chemistry, Altai State Technical University, 46 Lenin Ave., 656038 Barnaul, RussiaPyrazole and benzotriazole-containing thioethers, namely 1,5-bis(3,5-dimethylpyrazol-1-yl)-3-thiapentane, 1,8-bis(3,5-dimethylpyrazol-1-yl)-3,6-dithiaoctane and 1,3-bis(1,2,3-benzotriazol-1-yl)-2-thiapropane were prepared and fully characterized. Oxidation of the pyrazole-containing thioether by hydrogen peroxide proceeds selectively to provide a sulfoxide or sulfone, depending on the amount of oxidant used. Oxidation of the benzotriazole derivative by hydrogen peroxide is not selective, and sulfoxide and sulfone form concurrently. Selenium dioxide-catalyzed oxidation of benzotriazole thioether by H2O2, however, proceeds selectively and yields sulfoxide only.https://doi.org/10.3762/bjoc.7.179azoleoxidationsulfonesulfoxidethioether |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Andrei S. Potapov Nina P. Chernova Vladimir D. Ogorodnikov Tatiana V. Petrenko Andrei I. Khlebnikov |
spellingShingle |
Andrei S. Potapov Nina P. Chernova Vladimir D. Ogorodnikov Tatiana V. Petrenko Andrei I. Khlebnikov Synthesis and oxidation of some azole-containing thioethers Beilstein Journal of Organic Chemistry azole oxidation sulfone sulfoxide thioether |
author_facet |
Andrei S. Potapov Nina P. Chernova Vladimir D. Ogorodnikov Tatiana V. Petrenko Andrei I. Khlebnikov |
author_sort |
Andrei S. Potapov |
title |
Synthesis and oxidation of some azole-containing thioethers |
title_short |
Synthesis and oxidation of some azole-containing thioethers |
title_full |
Synthesis and oxidation of some azole-containing thioethers |
title_fullStr |
Synthesis and oxidation of some azole-containing thioethers |
title_full_unstemmed |
Synthesis and oxidation of some azole-containing thioethers |
title_sort |
synthesis and oxidation of some azole-containing thioethers |
publisher |
Beilstein-Institut |
series |
Beilstein Journal of Organic Chemistry |
issn |
1860-5397 |
publishDate |
2011-11-01 |
description |
Pyrazole and benzotriazole-containing thioethers, namely 1,5-bis(3,5-dimethylpyrazol-1-yl)-3-thiapentane, 1,8-bis(3,5-dimethylpyrazol-1-yl)-3,6-dithiaoctane and 1,3-bis(1,2,3-benzotriazol-1-yl)-2-thiapropane were prepared and fully characterized. Oxidation of the pyrazole-containing thioether by hydrogen peroxide proceeds selectively to provide a sulfoxide or sulfone, depending on the amount of oxidant used. Oxidation of the benzotriazole derivative by hydrogen peroxide is not selective, and sulfoxide and sulfone form concurrently. Selenium dioxide-catalyzed oxidation of benzotriazole thioether by H2O2, however, proceeds selectively and yields sulfoxide only. |
topic |
azole oxidation sulfone sulfoxide thioether |
url |
https://doi.org/10.3762/bjoc.7.179 |
work_keys_str_mv |
AT andreispotapov synthesisandoxidationofsomeazolecontainingthioethers AT ninapchernova synthesisandoxidationofsomeazolecontainingthioethers AT vladimirdogorodnikov synthesisandoxidationofsomeazolecontainingthioethers AT tatianavpetrenko synthesisandoxidationofsomeazolecontainingthioethers AT andreiikhlebnikov synthesisandoxidationofsomeazolecontainingthioethers |
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1724305097919299584 |