Self-Organization of Pyrrole-Centered Pentaheterocyclic Ensembles in the Hetaryl Nitrile/Ethynyl Hetarene/KOBut/DMSO System

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Abstract

Pyrrole-centered pentaheterocyclic ensembles, tetrasubstituted 1H-pyrroles bearing fundamental heterocycles (pyrrole, furan, thiophene, pyridine) as substituents in various combinations, were synthesized in up to 60% yield by the interaction of hetarylnitriles with ethynylhetarenes in the KOBut/DMSO system (room temperature, 1 h). The synthesis is a cascade self-organization of three molecules of ethynylhetarene and one molecule of hetarylnitrile, triggered and driven by acetylenic carbanions.

About the authors

E. Yu Schmidt

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

ORCID iD: 0000-0002-0188-3015
Irkutsk, Russia

N. A Lobanova

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

ORCID iD: 0000-0003-4594-1034
Irkutsk, Russia

I. V Tatarinova

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

ORCID iD: 0000-0001-6237-8533
Irkutsk, Russia

I. A Ushakov

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

ORCID iD: 0000-0003-0176-1699
Irkutsk, Russia

B. A Trofimov

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: boris_trofimov@irioch.irk.ru
ORCID iD: 0000-0002-0430-3215
Irkutsk, Russia

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