Abstract: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.
Citation:
I. A. Bidusenko, E. Yu. Schmidt, N. I. Protsuk, I. A. Ushakov, B. A. Trofimov, “Diversifying the superbase-catalyzed C=N bond ethynylation: triaryl-1-pyrrolines and triaryl-1H-pyrroles from N-benzyl aldimines and arylacetylenes”, Mendeleev Commun., 33:1 (2023), 24–26
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This publication is cited in the following 7 articles:
P. A. Volkov, K. O. Khrapova, E. M. Vyi, A. A. Telezhkin, I. A. Bidusenko, A. I. Albanov, A. V. Shchepochkin, Mendeleev Commun., 35:1 (2025), 102–104
Ivan A. Bidusenko, Elena Yu. Schmidt, Darya O. Kozlova, Nadezhda I. Protsuk, Igor A. Ushakov, Irina Yu. Bagryanskaya, Vladimir B. Orel, Andrey A. Zubarev, Boris A. Trofimov, “Tetraaryl-3H-Azepines: KOBut/DMSO-Catalyzed Assembly from Diaryldiynes and N-Benzylaldimines”, Org. Lett., 26:23 (2024), 4963
E. Yu. Schmidt, B. A. Trofimov, “Reaction of acetylenic carbanions with C=N bond: dynamics of development, synthetic divergence, environmental safety”, Russian Chem. Reviews, 93:10 (2024), RCR5145
I. A. Bidusenko, E. Yu. Schmidt, N. I. Protsuk, I. A. Ushakov, B. A. Trofimov, “The reaction of acetylenes with aldazines in the NaOBut/DMSO system: a contribution to the pyrazole chemistry”, Mendeleev Commun., 34:1 (2024), 110–112
N. M. Vitkovskaya, V. B. Orel, V. B. Kobychev, A. S. Bobkov, “Quantum Chemical Investigations of the Mechanisms of Carbo- and Heterocycles Assemblies Based on Acetylenes Reactions in Superbasic Media”, Russ J Org Chem, 59:10 (2023), 1660
Vladimir B. Orel, Andrey A. Zubarev, Ivan A. Bidusenko, Igor A. Ushakov, Nadezhda M. Vitkovskaya, “Quantum-Chemical Study of the Assembly Mechanism of 1-Pyrrolines from N-Benzylaldimines and Arylacetylenes in KOtBu/DMSO Superbasic Medium”, J. Org. Chem., 88:11 (2023), 7058
N. M Vitkovskaya, V. B Orel, V. B Kobychev, A. S Bobkov, “Quantum chemical investigations of the mechanisms of carboand heterocycles assemblies based on acetylenes reactions in superbasic media”, Žurnal organičeskoj himii, 59:10 (2023), 1301
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