Rapid, room-temperature self-organization of polyarylated 1H-pyrroles from acetylenes and nitriles in the KOBut/DMSO system

Schmidt, Elena Yu.; Tatarinova, Inna V.; Lobanova, Natal'ya A.; Ushakov, Igor A.; Bagryanskaya, Irina Yu.; Trofimov, Boris A.

doi:10.1039/d3ob01311a

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2024

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Cited by 3 publications

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One‐Pot Synthesis of 2‐Substituted‐4,5‐dimethyloxazoles from Amides and Acetylene Gas in the KOH/MeOH/DMSO Catalytic Triad

Schmidt,

Semenova,

Ivanova

et al. 2024

Adv Synth Catal

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Pharmaceutically prospective 2‐substituted‐4,5‐dimethyloxazoles are synthesized in up to 58% yield via unprecedented cascade assembly of one molecule of primary amide with two molecules of acetylene gas in the KOH/MeOH/DMSO (90 oC, 2 h) catalytic triad. This oxazoles self‐organization demonstrates unexpected successful competition of with the alkaline hydrolysis of amides. The mechanism involving amide N‐vinylation, enamine‐imine isomerization, imine ethynylation and intramolecular О‐vinylation cascade sequence has been deduced and supported by quantum‐chemical calculations using the B2PLYP‐D3/6‐311+G**//B3LYP/6‐31+G* + IEF PCM (B3LYP/6‐31+G*) approach..

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