Nucleophilic Functionalization of 2-R-3-Nitropyridines as a Versatile Approach to Novel Fluorescent Molecules

A number of new 2-methyl- and 2-arylvinyl-3-nitropyridines were synthesized and their reactions with thiols were studied. It was found that 3-NO(2) tends to be selectively substituted under the action of sulfur nucleophiles in the presence of another nucleofuge in position 5. Correlations between th...

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Autores principales: Nikol’skiy, Vladislav V., Minyaev, Mikhail E., Bastrakov, Maxim A., Starosotnikov, Alexey M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9457606/
https://www.ncbi.nlm.nih.gov/pubmed/36080461
http://dx.doi.org/10.3390/molecules27175692
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author Nikol’skiy, Vladislav V.
Minyaev, Mikhail E.
Bastrakov, Maxim A.
Starosotnikov, Alexey M.
author_facet Nikol’skiy, Vladislav V.
Minyaev, Mikhail E.
Bastrakov, Maxim A.
Starosotnikov, Alexey M.
author_sort Nikol’skiy, Vladislav V.
collection PubMed
description A number of new 2-methyl- and 2-arylvinyl-3-nitropyridines were synthesized and their reactions with thiols were studied. It was found that 3-NO(2) tends to be selectively substituted under the action of sulfur nucleophiles in the presence of another nucleofuge in position 5. Correlations between the substitution pattern and regioselectivity as well as photophysical properties were established. Some synthesized compounds possessed a large Stokes shift.
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spelling pubmed-94576062022-09-09 Nucleophilic Functionalization of 2-R-3-Nitropyridines as a Versatile Approach to Novel Fluorescent Molecules Nikol’skiy, Vladislav V. Minyaev, Mikhail E. Bastrakov, Maxim A. Starosotnikov, Alexey M. Molecules Article A number of new 2-methyl- and 2-arylvinyl-3-nitropyridines were synthesized and their reactions with thiols were studied. It was found that 3-NO(2) tends to be selectively substituted under the action of sulfur nucleophiles in the presence of another nucleofuge in position 5. Correlations between the substitution pattern and regioselectivity as well as photophysical properties were established. Some synthesized compounds possessed a large Stokes shift. MDPI 2022-09-03 /pmc/articles/PMC9457606/ /pubmed/36080461 http://dx.doi.org/10.3390/molecules27175692 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Nikol’skiy, Vladislav V.
Minyaev, Mikhail E.
Bastrakov, Maxim A.
Starosotnikov, Alexey M.
Nucleophilic Functionalization of 2-R-3-Nitropyridines as a Versatile Approach to Novel Fluorescent Molecules
title Nucleophilic Functionalization of 2-R-3-Nitropyridines as a Versatile Approach to Novel Fluorescent Molecules
title_full Nucleophilic Functionalization of 2-R-3-Nitropyridines as a Versatile Approach to Novel Fluorescent Molecules
title_fullStr Nucleophilic Functionalization of 2-R-3-Nitropyridines as a Versatile Approach to Novel Fluorescent Molecules
title_full_unstemmed Nucleophilic Functionalization of 2-R-3-Nitropyridines as a Versatile Approach to Novel Fluorescent Molecules
title_short Nucleophilic Functionalization of 2-R-3-Nitropyridines as a Versatile Approach to Novel Fluorescent Molecules
title_sort nucleophilic functionalization of 2-r-3-nitropyridines as a versatile approach to novel fluorescent molecules
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9457606/
https://www.ncbi.nlm.nih.gov/pubmed/36080461
http://dx.doi.org/10.3390/molecules27175692
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