Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis

Reaction of linear conjugated enynones, 1,5-diarylpent-2-en-4-yn-1-ones [Ar(1)C≡CCH=CHC(=O)Ar(2)], with 3-oxo-3-phenylpropanenitrile (NCCH(2)COPh) in the presence of sodium methoxide MeONa as a base in MeOH at room temperature for 4–26 h affords polyfunctional δ-diketones as a product of regioselect...

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Autores principales: Igushkina, Anastasiya V., Golovanov, Alexander A., Vasilyev, Aleksander V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8877045/
https://www.ncbi.nlm.nih.gov/pubmed/35209045
http://dx.doi.org/10.3390/molecules27041256
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author Igushkina, Anastasiya V.
Golovanov, Alexander A.
Vasilyev, Aleksander V.
author_facet Igushkina, Anastasiya V.
Golovanov, Alexander A.
Vasilyev, Aleksander V.
author_sort Igushkina, Anastasiya V.
collection PubMed
description Reaction of linear conjugated enynones, 1,5-diarylpent-2-en-4-yn-1-ones [Ar(1)C≡CCH=CHC(=O)Ar(2)], with 3-oxo-3-phenylpropanenitrile (NCCH(2)COPh) in the presence of sodium methoxide MeONa as a base in MeOH at room temperature for 4–26 h affords polyfunctional δ-diketones as a product of regioselective Michael addition to the double carbon–carbon bond of starting enynones. The δ-diketones have been formed as mixtures of two diastereomers in a ratio of 2.5:1 in good general yields of 53–98%. A synthetic potential of the obtained δ-diketones has been demonstrated by heterocyclization with hydrazine into substututed 5,6-dihydro-4H-1,2-diazepine.
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spelling pubmed-88770452022-02-26 Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis Igushkina, Anastasiya V. Golovanov, Alexander A. Vasilyev, Aleksander V. Molecules Article Reaction of linear conjugated enynones, 1,5-diarylpent-2-en-4-yn-1-ones [Ar(1)C≡CCH=CHC(=O)Ar(2)], with 3-oxo-3-phenylpropanenitrile (NCCH(2)COPh) in the presence of sodium methoxide MeONa as a base in MeOH at room temperature for 4–26 h affords polyfunctional δ-diketones as a product of regioselective Michael addition to the double carbon–carbon bond of starting enynones. The δ-diketones have been formed as mixtures of two diastereomers in a ratio of 2.5:1 in good general yields of 53–98%. A synthetic potential of the obtained δ-diketones has been demonstrated by heterocyclization with hydrazine into substututed 5,6-dihydro-4H-1,2-diazepine. MDPI 2022-02-13 /pmc/articles/PMC8877045/ /pubmed/35209045 http://dx.doi.org/10.3390/molecules27041256 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
Igushkina, Anastasiya V.
Golovanov, Alexander A.
Vasilyev, Aleksander V.
Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis
title Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis
title_full Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis
title_fullStr Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis
title_full_unstemmed Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis
title_short Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis
title_sort michael addition of 3-oxo-3-phenylpropanenitrile to linear conjugated enynones: approach to polyfunctional δ-diketones as precursors for heterocycle synthesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8877045/
https://www.ncbi.nlm.nih.gov/pubmed/35209045
http://dx.doi.org/10.3390/molecules27041256
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