Open Access
5-Chloroisoxazoles: A Versatile Starting Material for the Preparation of Amides, Anhydrides, Esters, and Thioesters of 2H-Azirine-2-carboxylic Acids
Тип публикации: Journal Article
Дата публикации: 2022-12-29
PubMed ID:
36615468
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Краткое описание
Amides, anhydrides, esters, and thioesters of 2H-azirine-2-carboxylic acids were prepared by a rapid procedure at room temperature involving FeCl2-catalyzed isomerization of 5-chloroisoxazoles to 2H-azirine-2-carbonyl chlorides, followed by reaction with N-, O-, or S-nucleophiles mediated by an ortho-substituted pyridine. With readily available chloroisoxazoles and a nucleophile, 2-picoline can be used as an inexpensive base. When a high yield of the acylation product is important, the reagent 2-(trimethylsilyl)pyridine/ethyl chloroformate is more suitable for the acylation with 2H-azirine-2-carbonyl chlorides.
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Agafonova A. V., Novikov M. S., Khlebnikov A. F. 5-Chloroisoxazoles: A Versatile Starting Material for the Preparation of Amides, Anhydrides, Esters, and Thioesters of 2H-Azirine-2-carboxylic Acids // Molecules. 2022. Vol. 28. No. 1. p. 275.
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Agafonova A. V., Novikov M. S., Khlebnikov A. F. 5-Chloroisoxazoles: A Versatile Starting Material for the Preparation of Amides, Anhydrides, Esters, and Thioesters of 2H-Azirine-2-carboxylic Acids // Molecules. 2022. Vol. 28. No. 1. p. 275.
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TY - JOUR
DO - 10.3390/molecules28010275
UR - https://www.mdpi.com/1420-3049/28/1/275
TI - 5-Chloroisoxazoles: A Versatile Starting Material for the Preparation of Amides, Anhydrides, Esters, and Thioesters of 2H-Azirine-2-carboxylic Acids
T2 - Molecules
AU - Agafonova, Anastasiya V
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
PY - 2022
DA - 2022/12/29
PB - MDPI
SP - 275
IS - 1
VL - 28
PMID - 36615468
SN - 1420-3049
ER -
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@article{2022_Agafonova,
author = {Anastasiya V Agafonova and Mikhail S. Novikov and Alexander F Khlebnikov},
title = {5-Chloroisoxazoles: A Versatile Starting Material for the Preparation of Amides, Anhydrides, Esters, and Thioesters of 2H-Azirine-2-carboxylic Acids},
journal = {Molecules},
year = {2022},
volume = {28},
publisher = {MDPI},
month = {dec},
url = {https://www.mdpi.com/1420-3049/28/1/275},
number = {1},
pages = {275},
doi = {10.3390/molecules28010275}
}
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Agafonova, Anastasiya V., et al. “5-Chloroisoxazoles: A Versatile Starting Material for the Preparation of Amides, Anhydrides, Esters, and Thioesters of 2H-Azirine-2-carboxylic Acids.” Molecules, vol. 28, no. 1, Dec. 2022, p. 275. https://www.mdpi.com/1420-3049/28/1/275.