Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates
Herein, we present the synthesis and utilization of derivatives of 4H-benzo[b][1,4]thiazine-3-carboxylic acid. These benzothiazine compounds were assembled via the coupling of aminothiols and bromopyruvates. Oxidative dimerization of these starting materials was also observed and the corresponding b...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2022-09-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.18.124 |
| _version_ | 1818021461018804224 |
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| author | Péter Kisszékelyi Tibor Peňaška Klára Stankovianska Mária Mečiarová Radovan Šebesta |
| author_facet | Péter Kisszékelyi Tibor Peňaška Klára Stankovianska Mária Mečiarová Radovan Šebesta |
| author_sort | Péter Kisszékelyi |
| collection | DOAJ |
| description | Herein, we present the synthesis and utilization of derivatives of 4H-benzo[b][1,4]thiazine-3-carboxylic acid. These benzothiazine compounds were assembled via the coupling of aminothiols and bromopyruvates. Oxidative dimerization of these starting materials was also observed and the corresponding benzothiazine dimers were isolated. Moreover, the coupling of benzothiazines with amino acids was realized. In doing so, an enantioselective synthesis of the nonproteinogenic amino acid 2-amino-3-propylhexanoic acid was accomplished. |
| first_indexed | 2024-04-14T08:19:13Z |
| format | Article |
| id | doaj.art-4c0256a1d5114eb889c8113619511f23 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-04-14T08:19:13Z |
| publishDate | 2022-09-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-4c0256a1d5114eb889c8113619511f232022-12-22T02:04:18ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-09-011811195120210.3762/bjoc.18.1241860-5397-18-124Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugatesPéter Kisszékelyi0Tibor Peňaška1Klára Stankovianska2Mária Mečiarová3Radovan Šebesta4Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia Herein, we present the synthesis and utilization of derivatives of 4H-benzo[b][1,4]thiazine-3-carboxylic acid. These benzothiazine compounds were assembled via the coupling of aminothiols and bromopyruvates. Oxidative dimerization of these starting materials was also observed and the corresponding benzothiazine dimers were isolated. Moreover, the coupling of benzothiazines with amino acids was realized. In doing so, an enantioselective synthesis of the nonproteinogenic amino acid 2-amino-3-propylhexanoic acid was accomplished.https://doi.org/10.3762/bjoc.18.124amino acidbenzothiazineoxidative dimerizationpeptide couplingstereoselective hydrogenation |
| spellingShingle | Péter Kisszékelyi Tibor Peňaška Klára Stankovianska Mária Mečiarová Radovan Šebesta Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates Beilstein Journal of Organic Chemistry amino acid benzothiazine oxidative dimerization peptide coupling stereoselective hydrogenation |
| title | Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates |
| title_full | Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates |
| title_fullStr | Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates |
| title_full_unstemmed | Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates |
| title_short | Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates |
| title_sort | derivatives of benzo 1 4 thiazine 3 carboxylic acid and the corresponding amino acid conjugates |
| topic | amino acid benzothiazine oxidative dimerization peptide coupling stereoselective hydrogenation |
| url | https://doi.org/10.3762/bjoc.18.124 |
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