Dihydropyrrole-3-thiones: one-pot synthesis from propargylamines, acyl chlorides and sodium sulfide.

Autor: Volkov PA; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation. boris_trofimov@irioch.irk.ru., Khrapova KO; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation. boris_trofimov@irioch.irk.ru., Vyi EM; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation. boris_trofimov@irioch.irk.ru., Telezhkin AA; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation. boris_trofimov@irioch.irk.ru., Bidusenko IA; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation. boris_trofimov@irioch.irk.ru., Albanov AI; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation. boris_trofimov@irioch.irk.ru., Schmidt EY; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation. boris_trofimov@irioch.irk.ru., Trofimov BA; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation. boris_trofimov@irioch.irk.ru.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2023 Aug 30; Vol. 21 (34), pp. 6903-6913. Date of Electronic Publication: 2023 Aug 30.
DOI: 10.1039/d3ob01061a
Abstrakt: An efficient one-pot synthesis of 1,2,5-trisubstituted-1,2-dihydro-3 H -pyrrole-3-thiones (up to 91% yield), representatives of essentially new heterocyclic systems, by the successive treatment of available propargylamines with acyl chlorides (PdCl 2 /CuI/Ph 3 P/Et 3 N, toluene, 40-45 °C, 3 h) and sodium sulfide (Na 2 S·9H 2 O, 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.
Databáze: MEDLINE