Rapid, room-temperature self-organization of polyarylated 1H-pyrroles from acetylenes and nitriles in the KOBut/DMSO system
Elena Yu. Schmidt
1
,
Inna Tatarinova
1
,
Natalya A Lobanova
1
,
Igor A. Ushakov
1
,
Irina Yu. Bagryanskaya
2
,
Publication type: Journal Article
Publication date: 2023-08-19
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
37642476
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
We have discovered that three molecules of arylacetylene are rapidly (15 min) assembled with one molecule of nitrile at room temperature in the KOBut/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 CN, then to the CC and CC 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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9
Total citations:
9
Citations from 2025:
6
(66.67%)
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GOST
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Schmidt E. Y. et al. Rapid, room-temperature self-organization of polyarylated 1H-pyrroles from acetylenes and nitriles in the KOBut/DMSO system // Organic and Biomolecular Chemistry. 2023. Vol. 21. No. 35. pp. 7209-7218.
GOST all authors (up to 50)
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Schmidt E. Y., Tatarinova I., Lobanova N. A., Ushakov I. A., Bagryanskaya I. Y., Trofimov B. A. Rapid, room-temperature self-organization of polyarylated 1H-pyrroles from acetylenes and nitriles in the KOBut/DMSO system // Organic and Biomolecular Chemistry. 2023. Vol. 21. No. 35. pp. 7209-7218.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/d3ob01311a
UR - https://xlink.rsc.org/?DOI=D3OB01311A
TI - Rapid, room-temperature self-organization of polyarylated 1H-pyrroles from acetylenes and nitriles in the KOBut/DMSO system
T2 - Organic and Biomolecular Chemistry
AU - Schmidt, Elena Yu.
AU - Tatarinova, Inna
AU - Lobanova, Natalya A
AU - Ushakov, Igor A.
AU - Bagryanskaya, Irina Yu.
AU - Trofimov, B. A.
PY - 2023
DA - 2023/08/19
PB - Royal Society of Chemistry (RSC)
SP - 7209-7218
IS - 35
VL - 21
PMID - 37642476
SN - 1477-0520
SN - 1477-0539
ER -
Cite this
BibTex (up to 50 authors)
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@article{2023_Schmidt,
author = {Elena Yu. Schmidt and Inna Tatarinova and Natalya A Lobanova and Igor A. Ushakov and Irina Yu. Bagryanskaya and B. A. Trofimov},
title = {Rapid, room-temperature self-organization of polyarylated 1H-pyrroles from acetylenes and nitriles in the KOBut/DMSO system},
journal = {Organic and Biomolecular Chemistry},
year = {2023},
volume = {21},
publisher = {Royal Society of Chemistry (RSC)},
month = {aug},
url = {https://xlink.rsc.org/?DOI=D3OB01311A},
number = {35},
pages = {7209--7218},
doi = {10.1039/d3ob01311a}
}
Cite this
MLA
Copy
Schmidt, Elena Yu., et al. “Rapid, room-temperature self-organization of polyarylated 1H-pyrroles from acetylenes and nitriles in the KOBut/DMSO system.” Organic and Biomolecular Chemistry, vol. 21, no. 35, Aug. 2023, pp. 7209-7218. https://xlink.rsc.org/?DOI=D3OB01311A.
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