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2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization
Reactions of 2-amino-1,3-benzothiazole with aliphatic, aromatic and heteroaromatic α-iodoketones in the absence of bases or catalysts have been studied. The reaction proceeds by N-alkylation of the endocyclic nitrogen atom followed by intramolecular dehydrative cyclization. The regioselectivity is e...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10004639/ https://www.ncbi.nlm.nih.gov/pubmed/36903340 http://dx.doi.org/10.3390/molecules28052093 |
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author | Dorofeev, Ivan A. Zhilitskaya, Larisa V. Yarosh, Nina O. Shainyan, Bagrat A. |
author_facet | Dorofeev, Ivan A. Zhilitskaya, Larisa V. Yarosh, Nina O. Shainyan, Bagrat A. |
author_sort | Dorofeev, Ivan A. |
collection | PubMed |
description | Reactions of 2-amino-1,3-benzothiazole with aliphatic, aromatic and heteroaromatic α-iodoketones in the absence of bases or catalysts have been studied. The reaction proceeds by N-alkylation of the endocyclic nitrogen atom followed by intramolecular dehydrative cyclization. The regioselectivity is explained and the mechanism of the reaction is proposed. A number of new linear and cyclic iodide and triiodide benzothiazolium salts have been obtained and their structure proved by NMR and UV spectroscopy. |
format | Online Article Text |
id | pubmed-10004639 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-100046392023-03-11 2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization Dorofeev, Ivan A. Zhilitskaya, Larisa V. Yarosh, Nina O. Shainyan, Bagrat A. Molecules Article Reactions of 2-amino-1,3-benzothiazole with aliphatic, aromatic and heteroaromatic α-iodoketones in the absence of bases or catalysts have been studied. The reaction proceeds by N-alkylation of the endocyclic nitrogen atom followed by intramolecular dehydrative cyclization. The regioselectivity is explained and the mechanism of the reaction is proposed. A number of new linear and cyclic iodide and triiodide benzothiazolium salts have been obtained and their structure proved by NMR and UV spectroscopy. MDPI 2023-02-23 /pmc/articles/PMC10004639/ /pubmed/36903340 http://dx.doi.org/10.3390/molecules28052093 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Dorofeev, Ivan A. Zhilitskaya, Larisa V. Yarosh, Nina O. Shainyan, Bagrat A. 2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization |
title | 2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization |
title_full | 2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization |
title_fullStr | 2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization |
title_full_unstemmed | 2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization |
title_short | 2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization |
title_sort | 2-amino-1,3-benzothiazole: endo n-alkylation with α-iodo methyl ketones followed by cyclization |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10004639/ https://www.ncbi.nlm.nih.gov/pubmed/36903340 http://dx.doi.org/10.3390/molecules28052093 |
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