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2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization
Publication type: Journal Article
Publication date: 2023-02-23
PubMed ID:
36903340
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
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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Dorofeev I. A. et al. 2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization // Molecules. 2023. Vol. 28. No. 5. p. 2093.
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Dorofeev I. A., Zhilitskaya L. V., Yarosh N. O., Shainyan B. A. 2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization // Molecules. 2023. Vol. 28. No. 5. p. 2093.
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TY - JOUR
DO - 10.3390/molecules28052093
UR - https://doi.org/10.3390/molecules28052093
TI - 2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization
T2 - Molecules
AU - Dorofeev, Ivan A.
AU - Zhilitskaya, Larisa V.
AU - Yarosh, Nina O.
AU - Shainyan, Bagrat A.
PY - 2023
DA - 2023/02/23
PB - MDPI
SP - 2093
IS - 5
VL - 28
PMID - 36903340
SN - 1420-3049
ER -
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@article{2023_Dorofeev,
author = {Ivan A. Dorofeev and Larisa V. Zhilitskaya and Nina O. Yarosh and Bagrat A. Shainyan},
title = {2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization},
journal = {Molecules},
year = {2023},
volume = {28},
publisher = {MDPI},
month = {feb},
url = {https://doi.org/10.3390/molecules28052093},
number = {5},
pages = {2093},
doi = {10.3390/molecules28052093}
}
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Dorofeev, Ivan A., et al. “2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization.” Molecules, vol. 28, no. 5, Feb. 2023, p. 2093. https://doi.org/10.3390/molecules28052093.