Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol
Two synthetic approaches to enaminones fused to 1,4-benzothiazin-2-one moiety, which can be interesting in studies on biological activity, chemosensors, and fluorescence, were developed via the reaction of furan-2,3-diones or acylpyruvic acids in the presence of carbodiimides with o-aminothiophenols...
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Online Access: | https://doi.org/10.3762/bjoc.16.193 |
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doaj-a604ea1e898a4b4098bb339e69e10d742021-04-02T18:10:25ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-09-011612322233110.3762/bjoc.16.1931860-5397-16-193Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenolEkaterina E. Stepanova0Maksim V. Dmitriev1Andrey N. Maslivets2Department of Chemistry, Perm State University, ul. Bukireva 15, Perm 614990, Russian FederationDepartment of Chemistry, Perm State University, ul. Bukireva 15, Perm 614990, Russian FederationDepartment of Chemistry, Perm State University, ul. Bukireva 15, Perm 614990, Russian FederationTwo synthetic approaches to enaminones fused to 1,4-benzothiazin-2-one moiety, which can be interesting in studies on biological activity, chemosensors, and fluorescence, were developed via the reaction of furan-2,3-diones or acylpyruvic acids in the presence of carbodiimides with o-aminothiophenols. The target enaminones were formed together with pharmaceutically interesting 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones. A selective synthetic approach to 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones was developed via the solvent-switchable reaction of furan-2,3-diones with o-aminothiophenol. Preliminary biological assays (antimicrobial, acute toxicity) of the new compounds were carried out.https://doi.org/10.3762/bjoc.16.193acylpyruvic acid1,4-benzothiazinecyclocondensationdiversity-oriented synthesisfuran-2,3-dione |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Ekaterina E. Stepanova Maksim V. Dmitriev Andrey N. Maslivets |
spellingShingle |
Ekaterina E. Stepanova Maksim V. Dmitriev Andrey N. Maslivets Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol Beilstein Journal of Organic Chemistry acylpyruvic acid 1,4-benzothiazine cyclocondensation diversity-oriented synthesis furan-2,3-dione |
author_facet |
Ekaterina E. Stepanova Maksim V. Dmitriev Andrey N. Maslivets |
author_sort |
Ekaterina E. Stepanova |
title |
Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol |
title_short |
Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol |
title_full |
Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol |
title_fullStr |
Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol |
title_full_unstemmed |
Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol |
title_sort |
synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol |
publisher |
Beilstein-Institut |
series |
Beilstein Journal of Organic Chemistry |
issn |
1860-5397 |
publishDate |
2020-09-01 |
description |
Two synthetic approaches to enaminones fused to 1,4-benzothiazin-2-one moiety, which can be interesting in studies on biological activity, chemosensors, and fluorescence, were developed via the reaction of furan-2,3-diones or acylpyruvic acids in the presence of carbodiimides with o-aminothiophenols. The target enaminones were formed together with pharmaceutically interesting 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones. A selective synthetic approach to 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones was developed via the solvent-switchable reaction of furan-2,3-diones with o-aminothiophenol. Preliminary biological assays (antimicrobial, acute toxicity) of the new compounds were carried out. |
topic |
acylpyruvic acid 1,4-benzothiazine cyclocondensation diversity-oriented synthesis furan-2,3-dione |
url |
https://doi.org/10.3762/bjoc.16.193 |
work_keys_str_mv |
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