Аннотация:
A new superbase-promoted reaction of acetylene involves self-organization of its three molecules with one molecule of arylamine in KOH/DMSO system to afford 1-aryl-2,5- dimethylpyrroles in up to 63% yields. The key step of this reaction cascade is assumed to be the nucleophilic addition of acetylene to the C=N bond of the intermediate aldimine (aza-Favorsky reaction).
Образец цитирования:
E. Yu. Schmidt, N. V. Semenova, E. V. Ivanova, I. A. Bidusenko, B. A. Trofimov, “Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles”, Mendeleev Commun., 30:1 (2020), 109–111
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc1117
https://www.mathnet.ru/rus/mendc/v30/i1/p109
Эта публикация цитируется в следующих 15 статьяx:
N. V. Semenova, I. A. Ushakov, E. Yu. Schmidt, B. A. Trofimov, “Reaction of 2-Aminobenzimidazoles with Acetylene in the KOBut/DMSO System. Self-Assembly of Benzo[d]imidazo[1,2-a]imidazoles and Benzo[4,5]imidazo[1,2-a]pyrimidines under Competition between Nucleophilic Centers”, Russ J Org Chem, 60:2 (2024), 353
E. Yu. Schmidt, N. A. Lobanova, I. V. Tatarinova, I. A. Ushakov, B. A. Trofimov, “Reaction of benzonitriles with acetylene in the KOBut/DMSO/THF system: self-organization of 2-aryl-3-ethynyl-4-aroyl-5-methylpyrroles and aminoacroleins”, Mendeleev Commun., 34:6 (2024), 868–870
Е. Ю. Шмидт, Б. А. Трофимов, “Реакция ацетиленовых карбанионов со связью C=N: динамика развития, синтетическая многовекторность, экологическая нейтральность”, Усп. хим., 93:10 (2024), RCR5145 ; 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
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
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
Damir Z. Absalyamov, Nadezhda M. Vitkovskaya, Vladimir B. Orel, Elena Yu. Schmidt, Boris A. Trofimov, “Quantum‐Chemical Insight into Self‐Organization of Complex Molecules from Acetylene and Anilines Catalyzed by Superbase KOH/DMSO: One‐Pot Cascade Assembly of 1,3‐Bis(arylamines)”, Asian J Org Chem, 12:4 (2023)
N. V. Semenova, E. Yu. Schmidt, I. A. Ushakov, B. A. Trofimov, “Acetylene-driven multi-molecular assemblies of high complexity: imidazo[1,2-a]pyridines and 5-chloro-N-[2-(imidazo[1,2-a]pyridin-6-yl)vinyl]pyridin-2-amine”, Mendeleev Commun., 33:2 (2023), 164–166
E. Yu. Schmidt, B. A. Trofimov, “Acetylene in Organic Synthesis. From the Chaos of Small Molecules to Highly Organized Structures. A Review”, Dokl Chem, 505:1 (2022), 127
K. P. Trainov, R. F. Salikov, A. Yu. Belyy, A. N. Kuznetsova, M. D. Khitrov, M. K. Ilyushchenko, A. D. Sokolova, D. N. Platonov, Yu. V. Tomilov, “Generation and cascade reactions of N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium species”, Mendeleev Commun., 32:2 (2022), 262–264
D Z Absalyamov, N M Vitkovskaya, “Quantum-chemical description of interactions in the PhNH2/HCCH system in a superbasic medium”, J. Phys.: Conf. Ser., 1847:1 (2021), 012049
Elena Yu. Schmidt, Nadezhda V. Semenova, Igor A. Ushakov, Alexander V. Vashchenko, Boris A. Trofimov, “Multimolecular Self-Organization of 1-Acetyl-1,3-bis(haloarylamines) in KOH/DMSO System: From Acetylene Gas and o-Halo Arylamines toward a Higher Molecular Complexity and Diversity”, Org. Lett., 23:12 (2021), 4743
Asieh Azhdari, Najmedin Azizi, Haleh Sanaeishoar, Elham Tahanpesar, “Amidosulfonic acid supported on graphitic carbon nitride: novel and straightforward catalyst for Paal–Knorr pyrrole reaction under mild conditions”, Monatsh Chem, 152:6 (2021), 625
Nadezhda M. Vitkovskaya, Vladimir B. Orel, Damir Z. Absalyamov, Boris A. Trofimov, “Self-Assembly of N-Phenyl-2,5-dimethylpyrrole from Acetylene and Aniline in KOH/DMSO and KOBut/DMSO Superbase Systems: A Quantum-Chemical Insight”, J. Org. Chem., 85:16 (2020), 10617
E. Yu. Schmidt, N. V. Semenova, E. V. Ivanova, I. A. Ushakov, B. A. Trofimov, “Multimolecular self-organization of acetylene and arylamines into 1-aryl-3-ethyl-4-vinylpyrroles in the KOBut/DMSO system”, Mendeleev Commun., 30:3 (2020), 315–317
L. A. Oparina, N. A. Kolyvanov, N. K. Gusarova, B. A. Trofimov, “Chemoselective vinylation of aminophenols with acetylene catalyzed by sodium aminophenolates in aqueous DMSO”, Mendeleev Commun., 30:6 (2020), 788–790
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