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Lithium-Promoted Cycloaddition of Indole-2,3-dienolates and Carbon Disulfide as a One-Pot Route to Thiopyrano[4,3-b]indole-3(5H)-thiones.
Suzdalev, Konstantin F; Vyalyh, Julia V; Tkachev, Valery V; Lysenko, Ekaterina A; Burov, Oleg N; Lisovin, Anton V; Kletskii, Mikhail E; Kurbatov, Sergey V.
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  • Suzdalev KF; Department of Chemistry, Southern Federal University, Rostov-on-Don 344090, Russia.
  • Vyalyh JV; Department of Chemistry, Southern Federal University, Rostov-on-Don 344090, Russia.
  • Tkachev VV; Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka 142432, Russia.
  • Lysenko EA; Department of Chemistry, Southern Federal University, Rostov-on-Don 344090, Russia.
  • Burov ON; Department of Chemistry, Southern Federal University, Rostov-on-Don 344090, Russia.
  • Lisovin AV; Department of Chemistry, Southern Federal University, Rostov-on-Don 344090, Russia.
  • Kletskii ME; Department of Chemistry, Southern Federal University, Rostov-on-Don 344090, Russia.
  • Kurbatov SV; Department of Chemistry, Southern Federal University, Rostov-on-Don 344090, Russia.
J Org Chem ; 86(17): 11698-11707, 2021 09 03.
Article en En | MEDLINE | ID: mdl-34338514
A new approach for the annulation of a thiopyrane ring to an indole core under mild conditions was developed. Treating 2-methyl-3-acylindoles with lithium diisopropyl amide leads to the elimination of a proton from the 2-methyl group. The lithium indole-2,3-dienolates obtained were found to react with CS2 to give the corresponding thiopyrano[4,3-b]indole-3(5H)-thiones. The mechanism represents a stepwise addition through ion-pair formation, according to PCM/B3LYP/6-311++G**, PBE1PBE/6-311++G**, and MP2//HF/6-311++G** quantum chemical calculations. AIM calculations revealed the essential role of the Li atom at all stages of the process.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Tionas / Disulfuro de Carbono Idioma: En Revista: J Org Chem Año: 2021 Tipo del documento: Article País de afiliación: Rusia Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Tionas / Disulfuro de Carbono Idioma: En Revista: J Org Chem Año: 2021 Tipo del documento: Article País de afiliación: Rusia Pais de publicación: Estados Unidos