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Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles

The reaction of 3,3-diaminoacrylonitriles with DMAD and 1,2-dibenzoylacetylene was studied. It is shown that the direction of the reaction depends on the structure both of acetylene and of diaminoacrylonitrile. In the reaction of DMAD with acrylonitriles bearing a monosubstituted amidine group, 1-su...

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Autores principales: Silaichev, Pavel S., Dianova, Lidia N., Beryozkina, Tetyana V., Berseneva, Vera S., Maslivets, Andrey N., Bakulev, Vasiliy A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10141133/
https://www.ncbi.nlm.nih.gov/pubmed/37110809
http://dx.doi.org/10.3390/molecules28083576
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author Silaichev, Pavel S.
Dianova, Lidia N.
Beryozkina, Tetyana V.
Berseneva, Vera S.
Maslivets, Andrey N.
Bakulev, Vasiliy A.
author_facet Silaichev, Pavel S.
Dianova, Lidia N.
Beryozkina, Tetyana V.
Berseneva, Vera S.
Maslivets, Andrey N.
Bakulev, Vasiliy A.
author_sort Silaichev, Pavel S.
collection PubMed
description The reaction of 3,3-diaminoacrylonitriles with DMAD and 1,2-dibenzoylacetylene was studied. It is shown that the direction of the reaction depends on the structure both of acetylene and of diaminoacrylonitrile. In the reaction of DMAD with acrylonitriles bearing a monosubstituted amidine group, 1-substituted 5-amino-2-oxo-pyrrole-3(2H)ylidenes are formed. On the other hand, a similar reaction of acrylonitriles containing the N,N-dialkylamidine group affords 1-NH-5-aminopyrroles. In both cases, pyrroles containing two exocyclic double bonds are formed in high yields. A radically different type of pyrroles containing one exocyclic C=C bond and sp(3) hybrid carbon in the cycle is formed in reactions of 3,3-diaminoacrylonitriles with 1,2-diaroylacetylenes. As in reactions with DMAD, the interaction of 3,3-diaminoacrylonitriles with 1,2-dibenzoylacetylene can lead, depending on the structure of the amidine fragment, both to NH- and 1-substituted pyrroles. The formation of the obtained pyrrole derivatives is explained by the proposed mechanisms of the studied reactions.
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spelling pubmed-101411332023-04-29 Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles Silaichev, Pavel S. Dianova, Lidia N. Beryozkina, Tetyana V. Berseneva, Vera S. Maslivets, Andrey N. Bakulev, Vasiliy A. Molecules Article The reaction of 3,3-diaminoacrylonitriles with DMAD and 1,2-dibenzoylacetylene was studied. It is shown that the direction of the reaction depends on the structure both of acetylene and of diaminoacrylonitrile. In the reaction of DMAD with acrylonitriles bearing a monosubstituted amidine group, 1-substituted 5-amino-2-oxo-pyrrole-3(2H)ylidenes are formed. On the other hand, a similar reaction of acrylonitriles containing the N,N-dialkylamidine group affords 1-NH-5-aminopyrroles. In both cases, pyrroles containing two exocyclic double bonds are formed in high yields. A radically different type of pyrroles containing one exocyclic C=C bond and sp(3) hybrid carbon in the cycle is formed in reactions of 3,3-diaminoacrylonitriles with 1,2-diaroylacetylenes. As in reactions with DMAD, the interaction of 3,3-diaminoacrylonitriles with 1,2-dibenzoylacetylene can lead, depending on the structure of the amidine fragment, both to NH- and 1-substituted pyrroles. The formation of the obtained pyrrole derivatives is explained by the proposed mechanisms of the studied reactions. MDPI 2023-04-19 /pmc/articles/PMC10141133/ /pubmed/37110809 http://dx.doi.org/10.3390/molecules28083576 Text en © 2023 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
Silaichev, Pavel S.
Dianova, Lidia N.
Beryozkina, Tetyana V.
Berseneva, Vera S.
Maslivets, Andrey N.
Bakulev, Vasiliy A.
Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles
title Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles
title_full Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles
title_fullStr Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles
title_full_unstemmed Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles
title_short Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles
title_sort synthesis of non-aromatic pyrroles based on the reaction of carbonyl derivatives of acetylene with 3,3-diaminoacrylonitriles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10141133/
https://www.ncbi.nlm.nih.gov/pubmed/37110809
http://dx.doi.org/10.3390/molecules28083576
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