Diversifying the superbase-catalyzed C=N bond ethynylation: triaryl-1-pyrrolines and triaryl-1H-pyrroles from N-benzyl aldimines and arylacetylenes

[Display omitted] N-Benzyl aldimines react with arylacetylenes in the presence of ButOK/DMSO superbase system to afford 2,3,5-triaryl-1-pyrrolines as two tautomers with 1,2- and 1,5-location of the double bond, both being the trans-diastereomers. This version of the C=N bond ethynylation differs fro...

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Bibliographic Details
Published in:Mendeleev communications 2023-01, Vol.33 (1), p.24-26
Main Authors: Bidusenko, Ivan A., Yu. Schmidt, Elena, Protsuk, Nadezhda I., Ushakov, Igor A., Trofimov, Boris A.
Format: Article
Language:English
Subjects:
acetylenes
ethynylation
imines
pyrroles
pyrrolines
superbases
vinylation
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Summary:[Display omitted] N-Benzyl aldimines react with arylacetylenes in the presence of ButOK/DMSO superbase system to afford 2,3,5-triaryl-1-pyrrolines as two tautomers with 1,2- and 1,5-location of the double bond, both being the trans-diastereomers. This version of the C=N bond ethynylation differs from the previous one with N-benzyl ketimines. The oxidation of the pyrroline tautomeric mixtures without their isolation gives 2,3,5-triaryl-1H-pyrroles.
ISSN:0959-9436
DOI:10.1016/j.mencom.2023.01.007