Dihydropyrrole-3-thiones: one-pot synthesis from propargylamines, acyl chlorides and sodium sulfide
Publication type: Journal Article
Publication date: 2023-08-09
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
37581533
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
An efficient one-pot synthesis of 1,2,5-trisubstituted-1,2-dihydro-3H-pyrrole-3-thiones (up to 91% yield), representatives of essentially new heterocyclic systems, by the successive treatment of available propargylamines with acyl chlorides (PdCl2/CuI/Ph3P/Et3N, toluene, 40–45 °C, 3 h) and sodium sulfide (Na2S·9H2O, EtOH, 20–25 °C, 7 h) has been developed. The synthesis comprises the addition of sulfide anions to the formed aminoacetylenic ketones followed by dehydrative cyclization of the prototropically rearranged adducts.
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7
Total citations:
7
Citations from 2024:
7
(100%)
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Volkov P. A. et al. Dihydropyrrole-3-thiones: one-pot synthesis from propargylamines, acyl chlorides and sodium sulfide // Organic and Biomolecular Chemistry. 2023. Vol. 21. No. 34. pp. 6903-6913.
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Volkov P. A., Khrapova K. O., Vyi E. M., Telezhkin A. A., Bidusenko I. A., Albanov A. I., Schmidt E. Y., Trofimov B. A. Dihydropyrrole-3-thiones: one-pot synthesis from propargylamines, acyl chlorides and sodium sulfide // Organic and Biomolecular Chemistry. 2023. Vol. 21. No. 34. pp. 6903-6913.
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RIS
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TY - JOUR
DO - 10.1039/d3ob01061a
UR - https://xlink.rsc.org/?DOI=D3OB01061A
TI - Dihydropyrrole-3-thiones: one-pot synthesis from propargylamines, acyl chlorides and sodium sulfide
T2 - Organic and Biomolecular Chemistry
AU - Volkov, Pavel A.
AU - Khrapova, Kseniya O
AU - Vyi, Ekaterina M.
AU - Telezhkin, Anton A
AU - Bidusenko, Ivan A
AU - Albanov, Alexander I
AU - Schmidt, Elena Yu.
AU - Trofimov, B. A.
PY - 2023
DA - 2023/08/09
PB - Royal Society of Chemistry (RSC)
SP - 6903-6913
IS - 34
VL - 21
PMID - 37581533
SN - 1477-0520
SN - 1477-0539
ER -
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BibTex (up to 50 authors)
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@article{2023_Volkov,
author = {Pavel A. Volkov and Kseniya O Khrapova and Ekaterina M. Vyi and Anton A Telezhkin and Ivan A Bidusenko and Alexander I Albanov and Elena Yu. Schmidt and B. A. Trofimov},
title = {Dihydropyrrole-3-thiones: one-pot synthesis from propargylamines, acyl chlorides and sodium sulfide},
journal = {Organic and Biomolecular Chemistry},
year = {2023},
volume = {21},
publisher = {Royal Society of Chemistry (RSC)},
month = {aug},
url = {https://xlink.rsc.org/?DOI=D3OB01061A},
number = {34},
pages = {6903--6913},
doi = {10.1039/d3ob01061a}
}
Cite this
MLA
Copy
Volkov, Pavel A., et al. “Dihydropyrrole-3-thiones: one-pot synthesis from propargylamines, acyl chlorides and sodium sulfide.” Organic and Biomolecular Chemistry, vol. 21, no. 34, Aug. 2023, pp. 6903-6913. https://xlink.rsc.org/?DOI=D3OB01061A.
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