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...

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Autores principales: Dorofeev, Ivan A., Zhilitskaya, Larisa V., Yarosh, Nina O., Shainyan, Bagrat A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
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.
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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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