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volume 28 issue 5 pages 2093

2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization

Publication typeJournal Article
Publication date2023-02-23
scimago Q1
wos Q2
SJR0.865
CiteScore8.6
Impact factor4.6
ISSN14203049
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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
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BibTex (up to 50 authors) Copy
@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}
}
MLA
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MLA Copy
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.