Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles
Электронный научный архив УРФУ
Информация об архиве | Просмотр оригинала| Поле | Значение | |
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Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles
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| Автор |
Silaichev, P. S.
Dianova, L. N. Beryozkina, T. V. Berseneva, V. S. Maslivets, A. N. Bakulev, V. A. |
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| Тематика |
1,2-DIBENZOYLACETYLENE
3,3-DIAMINOACRYLONITRILES 5-AMINOPYRROLES ACETYLENEDICARBOXYLATE (DMAD) PYRROL-3(2H)-YLIDENE ACETATES |
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| Описание |
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 sp3 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. © 2023 by the authors.
Ministry of Education and Science of the Russian Federation, Minobrnauka: 4.71 The research funding from the Ministry of Science and Higher Education of the Russian Federation (Ural Federal University Program of Development within the Priority-2030 Program, grant №4.71) is gratefully acknowledged. |
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| Дата |
2024-04-05T16:20:57Z
2024-04-05T16:20:57Z 2023 |
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| Тип |
Article
Journal article (info:eu-repo/semantics/article) |info:eu-repo/semantics/publishedVersion |
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| Идентификатор |
Silaichev, PS, Dianova , LN, Beryozkina, TV, Berseneva, VS, Maslivets, AN & Bakulev , VA 2023, 'Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles', Molecules, Том. 28, № 8, 3576. https://doi.org/10.3390/molecules28083576
Silaichev, P. S., Dianova , L. N., Beryozkina, T. V., Berseneva, V. S., Maslivets, A. N., & Bakulev , V. A. (2023). Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles. Molecules, 28(8), [3576]. https://doi.org/10.3390/molecules28083576 1420-3049 Final All Open Access, Gold, Green https://www.scopus.com/inward/record.uri?eid=2-s2.0-85156105556&doi=10.3390%2fmolecules28083576&partnerID=40&md5=dc4c09463721e07fac08fd3b1638bc9a https://www.mdpi.com/1420-3049/28/8/3576/pdf?version=1681899733 http://elar.urfu.ru/handle/10995/130446 10.3390/molecules28083576 85156105556 000979049700001 |
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| Язык |
en
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| Права |
Open access (info:eu-repo/semantics/openAccess)
cc-by https://creativecommons.org/licenses/by/4.0/ |
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| Формат |
application/pdf
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MDPI
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| Источник |
Molecules
Molecules |
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