Open Access
Molecules, volume 26, issue 23, pages 7355
Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines
Shea Michael T
1
,
Rohde Gregory
2
,
Vlasenko Yulia A
3
,
Yusubov Mekhman S.
3
,
Saito Akio
4
,
YOSHIMURA Akira
1, 3
1
Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA
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2
Marshall School, Duluth, MN 55811, USA
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4
Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, Tokyo 184-8588, Japan
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Publication type: Journal Article
Publication date: 2021-12-03
PubMed ID:
34885939
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
Hypervalent iodine heterocycles represent one of the important classes of hypervalent iodine reagents with many applications in organic synthesis. This paper reports a simple and convenient synthesis of benziodazolones by the reaction of readily available iodobenzamides with m-chloroperoxybenzoic acid in acetonitrile at room temperature. The structure of one of these new iodine heterocycles was confirmed by X-ray analysis. In combination with PPh3 and pyridine, these benziodazolones can smoothly react with alcohols or amines to produce the corresponding esters or amides of 3-chlorobenzoic acid, respectively. It was found that the novel benziodazolone reagent reacts more efficiently than the analogous benziodoxolone reagent in this esterification.
Citations by journals
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1
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Advanced Synthesis and Catalysis
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Advanced Synthesis and Catalysis
1 publication, 50%
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Chemical Communications
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Chemical Communications
1 publication, 50%
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1
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Citations by publishers
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1
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Wiley
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Wiley
1 publication, 50%
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 50%
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1
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GOST
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Shea M. T. et al. Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines // Molecules. 2021. Vol. 26. No. 23. p. 7355.
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Shea M. T., Rohde G., Vlasenko Y. A., Postnikov P. S., Yusubov M. S., Zhdankin V. V., Saito A., YOSHIMURA A. Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines // Molecules. 2021. Vol. 26. No. 23. p. 7355.
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RIS
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TY - JOUR
DO - 10.3390/molecules26237355
UR - https://doi.org/10.3390%2Fmolecules26237355
TI - Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines
T2 - Molecules
AU - Shea, Michael T
AU - Vlasenko, Yulia A
AU - Yusubov, Mekhman S.
AU - Rohde, Gregory
AU - Postnikov, Pavel S.
AU - Zhdankin, Viktor V.
AU - Saito, Akio
AU - YOSHIMURA, Akira
PY - 2021
DA - 2021/12/03 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 7355
IS - 23
VL - 26
PMID - 34885939
SN - 1420-3049
ER -
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@article{2021_Shea,
author = {Michael T Shea and Yulia A Vlasenko and Mekhman S. Yusubov and Gregory Rohde and Pavel S. Postnikov and Viktor V. Zhdankin and Akio Saito and Akira YOSHIMURA},
title = {Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines},
journal = {Molecules},
year = {2021},
volume = {26},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {dec},
url = {https://doi.org/10.3390%2Fmolecules26237355},
number = {23},
pages = {7355},
doi = {10.3390/molecules26237355}
}
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MLA
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Shea, Michael T., et al. “Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines.” Molecules, vol. 26, no. 23, Dec. 2021, p. 7355. https://doi.org/10.3390%2Fmolecules26237355.