Microwave-Assisted Synthesis of Fluorescent Pyrido[2,3-b]indolizines from Alkylpyridinium Salts and Enaminones

Pyridinium ylides are well recognized as dipoles for cycloaddition reactions. In its turn, the microwave-assisted interaction of N-(cyanomethyl)-2-alkylpyridinium salts with enaminones unexpectedly proceeds as a domino sequence of cycloisomerization and cyclocondensation reactions, instead of a 1,3-...

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Autores principales: Sokolova, Ekaterina A., Festa, Alexey A., Subramani, Karthikeyan, Rybakov, Victor B., Varlamov, Alexey V., Voskressensky, Leonid G., Van der Eycken, Erik V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7570714/
https://www.ncbi.nlm.nih.gov/pubmed/32899473
http://dx.doi.org/10.3390/molecules25184059
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author Sokolova, Ekaterina A.
Festa, Alexey A.
Subramani, Karthikeyan
Rybakov, Victor B.
Varlamov, Alexey V.
Voskressensky, Leonid G.
Van der Eycken, Erik V.
author_facet Sokolova, Ekaterina A.
Festa, Alexey A.
Subramani, Karthikeyan
Rybakov, Victor B.
Varlamov, Alexey V.
Voskressensky, Leonid G.
Van der Eycken, Erik V.
author_sort Sokolova, Ekaterina A.
collection PubMed
description Pyridinium ylides are well recognized as dipoles for cycloaddition reactions. In its turn, the microwave-assisted interaction of N-(cyanomethyl)-2-alkylpyridinium salts with enaminones unexpectedly proceeds as a domino sequence of cycloisomerization and cyclocondensation reactions, instead of a 1,3-dipolar cycloaddition. The reaction takes place in the presence of sodium acetate as base and employs benign solvents. The optical properties of the resulting pyrido[2,3-b]indolizines were studied, showing green light emission with high fluorescence quantum yields.
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spelling pubmed-75707142020-10-28 Microwave-Assisted Synthesis of Fluorescent Pyrido[2,3-b]indolizines from Alkylpyridinium Salts and Enaminones Sokolova, Ekaterina A. Festa, Alexey A. Subramani, Karthikeyan Rybakov, Victor B. Varlamov, Alexey V. Voskressensky, Leonid G. Van der Eycken, Erik V. Molecules Article Pyridinium ylides are well recognized as dipoles for cycloaddition reactions. In its turn, the microwave-assisted interaction of N-(cyanomethyl)-2-alkylpyridinium salts with enaminones unexpectedly proceeds as a domino sequence of cycloisomerization and cyclocondensation reactions, instead of a 1,3-dipolar cycloaddition. The reaction takes place in the presence of sodium acetate as base and employs benign solvents. The optical properties of the resulting pyrido[2,3-b]indolizines were studied, showing green light emission with high fluorescence quantum yields. MDPI 2020-09-05 /pmc/articles/PMC7570714/ /pubmed/32899473 http://dx.doi.org/10.3390/molecules25184059 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
Sokolova, Ekaterina A.
Festa, Alexey A.
Subramani, Karthikeyan
Rybakov, Victor B.
Varlamov, Alexey V.
Voskressensky, Leonid G.
Van der Eycken, Erik V.
Microwave-Assisted Synthesis of Fluorescent Pyrido[2,3-b]indolizines from Alkylpyridinium Salts and Enaminones
title Microwave-Assisted Synthesis of Fluorescent Pyrido[2,3-b]indolizines from Alkylpyridinium Salts and Enaminones
title_full Microwave-Assisted Synthesis of Fluorescent Pyrido[2,3-b]indolizines from Alkylpyridinium Salts and Enaminones
title_fullStr Microwave-Assisted Synthesis of Fluorescent Pyrido[2,3-b]indolizines from Alkylpyridinium Salts and Enaminones
title_full_unstemmed Microwave-Assisted Synthesis of Fluorescent Pyrido[2,3-b]indolizines from Alkylpyridinium Salts and Enaminones
title_short Microwave-Assisted Synthesis of Fluorescent Pyrido[2,3-b]indolizines from Alkylpyridinium Salts and Enaminones
title_sort microwave-assisted synthesis of fluorescent pyrido[2,3-b]indolizines from alkylpyridinium salts and enaminones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7570714/
https://www.ncbi.nlm.nih.gov/pubmed/32899473
http://dx.doi.org/10.3390/molecules25184059
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