Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines

A number of novel 6-R-isoxazolo[4,3-b]pyridines were synthesized and their reactions with neutral C-nucleophiles (1,3-dicarbonyl compounds, π-excessive (het)arenes, dienes) were studied. The reaction rate was found to be dependent on the nature of the substituent 6-R. The most reactive 6-nitroisoxaz...

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Autores principales: Bastrakov, Maxim A., Fedorenko, Alexey K., Starosotnikov, Alexey M., Fedyanin, Ivan V., Kokorekin, Vladimir A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7248838/
https://www.ncbi.nlm.nih.gov/pubmed/32397095
http://dx.doi.org/10.3390/molecules25092194
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author Bastrakov, Maxim A.
Fedorenko, Alexey K.
Starosotnikov, Alexey M.
Fedyanin, Ivan V.
Kokorekin, Vladimir A.
author_facet Bastrakov, Maxim A.
Fedorenko, Alexey K.
Starosotnikov, Alexey M.
Fedyanin, Ivan V.
Kokorekin, Vladimir A.
author_sort Bastrakov, Maxim A.
collection PubMed
description A number of novel 6-R-isoxazolo[4,3-b]pyridines were synthesized and their reactions with neutral C-nucleophiles (1,3-dicarbonyl compounds, π-excessive (het)arenes, dienes) were studied. The reaction rate was found to be dependent on the nature of the substituent 6-R. The most reactive 6-nitroisoxazolo[4,3-b]pyridines are able to add C-nucleophiles in the absence of a base under mild conditions. In addition, these compounds readily undergo [4+2]-cycloaddition reactions on aromatic bonds C=C(NO(2)) of the pyridine ring, thus indicating the superelectrophilic nature of 6-NO(2)-isoxazolo[4,3-b]pyridines.
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spelling pubmed-72488382020-06-10 Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines Bastrakov, Maxim A. Fedorenko, Alexey K. Starosotnikov, Alexey M. Fedyanin, Ivan V. Kokorekin, Vladimir A. Molecules Article A number of novel 6-R-isoxazolo[4,3-b]pyridines were synthesized and their reactions with neutral C-nucleophiles (1,3-dicarbonyl compounds, π-excessive (het)arenes, dienes) were studied. The reaction rate was found to be dependent on the nature of the substituent 6-R. The most reactive 6-nitroisoxazolo[4,3-b]pyridines are able to add C-nucleophiles in the absence of a base under mild conditions. In addition, these compounds readily undergo [4+2]-cycloaddition reactions on aromatic bonds C=C(NO(2)) of the pyridine ring, thus indicating the superelectrophilic nature of 6-NO(2)-isoxazolo[4,3-b]pyridines. MDPI 2020-05-08 /pmc/articles/PMC7248838/ /pubmed/32397095 http://dx.doi.org/10.3390/molecules25092194 Text en © 2020 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Bastrakov, Maxim A.
Fedorenko, Alexey K.
Starosotnikov, Alexey M.
Fedyanin, Ivan V.
Kokorekin, Vladimir A.
Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines
title Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines
title_full Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines
title_fullStr Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines
title_full_unstemmed Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines
title_short Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines
title_sort synthesis and facile dearomatization of highly electrophilic nitroisoxazolo[4,3-b]pyridines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7248838/
https://www.ncbi.nlm.nih.gov/pubmed/32397095
http://dx.doi.org/10.3390/molecules25092194
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