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Elemental sulfur as a trigger and reagent in cyclization of γ-amino acetylenic ketones to 1,2-dihydro-3H-pyrrole-3-thiones

Pavel Anatol'evich Volkov 1
Pavel Anatol'evich Volkov
, 
Kseniya Olegovna Khrapova 1
Kseniya Olegovna Khrapova
, 
Ekaterina Mikhaylovna Vyi 1
Ekaterina Mikhaylovna Vyi
, 
Anton Alekseevich Telezhkin 1
Anton Alekseevich Telezhkin
, 
Ivan A. Bidusenko 1
Ivan A. Bidusenko
, 
Alexander Ivanovich Albanov 1
Alexander Ivanovich Albanov
, 
Alexandr Vladimirovich Shchepochkin 2
Alexandr Vladimirovich Shchepochkin
1 A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
2 I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 620219 Ekaterinburg, Russian Federation
10.71267/mencom.7582
Published 2025-01-24
Communication , Volume 35, Issue 1, 102-104
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Volkov P. A. et al. Elemental sulfur as a trigger and reagent in cyclization of γ-amino acetylenic ketones to 1,2-dihydro-3H-pyrrole-3-thiones // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 102-104.
GOST all authors (up to 50) Copy
Volkov P. A., Khrapova K. O., Vyi E. M., Telezhkin A. A., Bidusenko I. A., Albanov A. I., Shchepochkin A. V. Elemental sulfur as a trigger and reagent in cyclization of γ-amino acetylenic ketones to 1,2-dihydro-3H-pyrrole-3-thiones // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 102-104.
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TY - JOUR
DO - 10.71267/mencom.7582
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7582
TI - Elemental sulfur as a trigger and reagent in cyclization of γ-amino acetylenic ketones to 1,2-dihydro-3H-pyrrole-3-thiones
T2 - Mendeleev Communications
AU - Volkov, Pavel Anatol'evich
AU - Khrapova, Kseniya Olegovna
AU - Vyi, Ekaterina Mikhaylovna
AU - Telezhkin, Anton Alekseevich
AU - Bidusenko, Ivan A.
AU - Albanov, Alexander Ivanovich
AU - Shchepochkin, Alexandr Vladimirovich
PY - 2025
DA - 2025/01/24
PB - Mendeleev Communications
SP - 102-104
IS - 1
VL - 35
ER -
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@article{2025_Volkov,
author = {Pavel Anatol'evich Volkov and Kseniya Olegovna Khrapova and Ekaterina Mikhaylovna Vyi and Anton Alekseevich Telezhkin and Ivan A. Bidusenko and Alexander Ivanovich Albanov and Alexandr Vladimirovich Shchepochkin},
title = {Elemental sulfur as a trigger and reagent in cyclization of γ-amino acetylenic ketones to 1,2-dihydro-3H-pyrrole-3-thiones},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7582},
number = {1},
pages = {102--104},
doi = {10.71267/mencom.7582}
}
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Volkov, Pavel Anatol'evich, et al. “Elemental sulfur as a trigger and reagent in cyclization of γ-amino acetylenic ketones to 1,2-dihydro-3H-pyrrole-3-thiones.” Mendeleev Communications, vol. 35, no. 1, Jan. 2025, pp. 102-104. https://mendcomm.colab.ws/publications/10.71267/mencom.7582.

Keywords

1
2-dihydro-3H-pyrrole-3-thiones
amino acetylenic ketones
elemental sulfur
heterocyclization
nucleophilic addition
potassium hydroxide.

Abstract

An original and effective synthesis of 1,2-dihydro-3H-pyrrole-3-thiones from available γ-amino acetylenic ketones and elemental sulfur as a trigger and reagent has been developed. The reaction is carried out in the KOH/ethanol system, the yield of the target heterocycles being 46-75%.

Funders

Ministry of Education and Science of the Russian Federation
121021000199-6

References

.
Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part 2.
Jiang T., Kuhen K.L., Wolff K., Yin H., Bieza K., Caldwell J., Bursulaya B., Wu T.Y., He Y.
Bioorganic and Medicinal Chemistry Letters, 2006
.
Reactions of triads Se8KOHDMSO, Se8KOHDMSO, TeKOHHMPA with acetylenes
Trofimov B.A., Amosova S.V., Gurasova N.K., Musorin G.K.
Tetrahedron, 1982
.
Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur
Meng L., Fujikawa T., Kuwayama M., Segawa Y., Itami K.
Journal of the American Chemical Society, 2016
.
Chemoselective cross-coupling of terminal propargylamines with (het)aroyl chlorides: synthesis of β-aminoacetylenic ketones bearing aromatic and heteroaromatic substituents
Volkov P.A., Khrapova K.O., Bidusenko I.A., Telezhkin A.A., Schmidt E.Y., Albanov A.I., Trofimov B.A.
Russian Chemical Bulletin, 2022
.
Pd/Cu‐catalyzed cross‐coupling of new densely substituted propargylamines with aromatic acyl chlorides followed by the treatment with a base: a robust access to dihydro‐3H‐pyrrol‐3‐ones
Volkov P.A., Khrapova K.O., Telezhkin A.A., Bidusenko I.A., Schmidt E.Y., Albanov A.I., Trofimov B.A.
Advanced Synthesis and Catalysis, 2022
.
The Ammosamides: Structures of Cell Cycle Modulators from a Marine-DerivedStreptomycesSpecies
Hughes C., MacMillan J., Gaudêncio S., Jensen P., Fenical W.
Angewandte Chemie - International Edition, 2009
.
Three-component reaction of imidazoles, cyanophenylacetylene, and chalcogens: stereoselective synthesis of 3-alkenyl-2-imidazolethiones and -selones
Belyaeva K.V., Andriyankova L.V., Nikitina L.P., Mal'kina A.G., Afonin A.V., Ushakov I.A., Bagryanskaya I.Y., Trofimov B.A.
Tetrahedron, 2014
.
Divinyl Sulfide: Synthesis, Properties, and Applications
Trofimov B.A., Amosova S.V.
Sulfur Reports, 1984
.
Unprecedented spirocyclization of 3-methyleneindoline-2-thiones during hydrolysis of the phytoalexin cyclobrassinin
Pedras M.S., Abdoli A., Chumala P.B., Saha P., Schatte G.
Bioorganic and Medicinal Chemistry Letters, 2013
.
Design, Synthesis, and Antiviral Evaluation of Some Polyhalogenated Indole C-nucleosides
Chen J.J., Wei Y., Williams J.D., Drach J.C., Townsend L.B.
Nucleosides, Nucleotides and Nucleic Acids, 2005
.
Dihydropyrrole-3-thiones: one-pot synthesis from propargylamines, acyl chlorides and sodium sulfide
Trofimov B., Volkov P., Khrapova K., Vyi E., Telezhkin A., Bidusenko I., Albanov A.I., Schmidt E.
Organic and Biomolecular Chemistry, 2023
.
Bidusenko I.A., Schmidt E.Y., Protsuk N.I., Ushakov I.A., Trofimov B.A.
Mendeleev Communications, 2024