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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Main Authors:	Andrei S. Potapov, Nina P. Chernova, Vladimir D. Ogorodnikov, Tatiana V. Petrenko, Andrei I. Khlebnikov
Format:	Article
Language:	English
Published:	Beilstein-Institut 2011-11-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	azole oxidation sulfone sulfoxide thioether
Online Access:	https://doi.org/10.3762/bjoc.7.179

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spelling	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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Synthesis and oxidation of some azole-containing thioethers

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