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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Autores principales: Kisszékelyi, Péter, Peňaška, Tibor, Stankovianska, Klára, Mečiarová, Mária, Šebesta, Radovan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9475188/
https://www.ncbi.nlm.nih.gov/pubmed/36128428
http://dx.doi.org/10.3762/bjoc.18.124
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author Kisszékelyi, Péter
Peňaška, Tibor
Stankovianska, Klára
Mečiarová, Mária
Šebesta, Radovan
author_facet Kisszékelyi, Péter
Peňaška, Tibor
Stankovianska, Klára
Mečiarová, Mária
Šebesta, Radovan
author_sort Kisszékelyi, Péter
collection PubMed
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.
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spelling pubmed-94751882022-09-19 Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates Kisszékelyi, Péter Peňaška, Tibor Stankovianska, Klára Mečiarová, Mária Šebesta, Radovan Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2022-09-09 /pmc/articles/PMC9475188/ /pubmed/36128428 http://dx.doi.org/10.3762/bjoc.18.124 Text en Copyright © 2022, Kisszékelyi et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Kisszékelyi, Péter
Peňaška, Tibor
Stankovianska, Klára
Mečiarová, Mária
Šebesta, Radovan
Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates
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 Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9475188/
https://www.ncbi.nlm.nih.gov/pubmed/36128428
http://dx.doi.org/10.3762/bjoc.18.124
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