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

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

doi:10.1039/D3OB01311A

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

Elena Yu. Schmidt,^a Inna V. Tatarinova,

^a Natal'ya A. Lobanova,

^a Igor A. Ushakov,^a Irina Yu. Bagryanskaya^b and Boris A. Trofimov

*^a

Author affiliations

* Corresponding authors

^a A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia
E-mail: boris_trofimov@irioch.irk.ru

^b N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090, Russia

Abstract

We have discovered that three molecules of arylacetylene are rapidly (15 min) assembled with one molecule of nitrile at room temperature in the KOBu^t/DMSO system to afford 2-aryl-3-arylethynyl-4-aryl-5-benzyl-1H-pyrroles in up to 76% yield. We assume that this unprecedented self-organization process involves the cascade addition of acetylenic carbanions, first to the C [triple bond, length as m-dash] N, then to the CC and C [double bond, length as m-dash] C bonds of the intermediates, followed by pyrrole ring closure via the intramolecular nucleophilic addition of the NH functional group to the CC bond of the final intermediates.

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Article information

DOI: https://doi.org/10.1039/D3OB01311A
Article type: Paper
Submitted: 25 Jul 2023
Accepted: 17 Aug 2023
First published: 19 Aug 2023

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Org. Biomol. Chem., 2023,21, 7209-7218

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

E. Yu. Schmidt, I. V. Tatarinova, N. A. Lobanova, I. A. Ushakov, I. Yu. Bagryanskaya and B. A. Trofimov, Org. Biomol. Chem., 2023, 21, 7209 DOI: 10.1039/D3OB01311A

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Organic & Biomolecular Chemistry