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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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2023-04, Vol.28 (8), p.3576
Main Authors: Silaichev, Pavel S, Dianova, Lidia N, Beryozkina, Tetyana V, Berseneva, Vera S, Maslivets, Andrey N, Bakulev, Vasiliy A
Format: Article
Language:English
Subjects:
1,2-dibenzoylacetylene
3,3-diaminoacrylonitriles
5-aminopyrroles
Acetylene
acetylenedicarboxylate (DMAD)
Acrylonitriles
Carbon
Carbonyl compounds
Carbonyls
Chemical bonds
Chemical properties
Data analysis
Ions
pyrrol-3(2H)-ylidene acetates
Pyrroles
Substitutes
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Summary: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(2 )ylidenes are formed. On the other hand, a similar reaction of acrylonitriles containing the , -dialkylamidine group affords 1- -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 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 - and 1-substituted pyrroles. The formation of the obtained pyrrole derivatives is explained by the proposed mechanisms of the studied reactions.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28083576