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Beilstein Journal of Organic ChemistryVolume 11, 11 June 2015, Pages 1000-1007

A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles(Article)(Open Access)

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  • aPostovsky Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences, Ekaterinburg, 620990, Russian Federation
  • bUral Federal University, Ekaterinburg, 620002, Russian Federation

Abstract

A short and robust approach for the synthesis of 2-(hetero)aryl substituted thieno[2,3-b]indoles from easily available 1-alkylisatins and acetylated (hetero)arenes has been advanced. The two-step procedure includes the "aldol-crotonic" type of condensation of the starting materials, followed by treatment of the intermediate 3-(2-oxo-2-(hetero)arylethylidene)indolin-2-ones with Lawesson's reagent. The latter process involves two sequential reactions, namely reduction of the C=C ethylidene double bond of the intermediate indolin-2-ones followed by the Paal-Knorr cyclization, thus affording tricyclic thieno[2,3-b]indoles. © 2015 Irgashev et al; licensee Beilstein-Institut.

Author keywords

Aldol-crotonic condensationIsatinLawesson's reagentMethyl ketonesPaal-Knorr reactionThieno[2,3-b]indole

Funding details

Funding sponsor Funding number Acronym
13-03-12434-ofi-m2,13-03-96049-r-ural-a,14-03-01017-A,15-03-00924-A
  • ISSN: 18605397
  • CODEN: BJOCB
  • Source Type: Journal
  • Original language: English
  • DOI: 10.3762/bjoc.11.112
  • Document Type: Article
  • Publisher: Beilstein-Institut Zur Forderung der Chemischen Wissenschaften

  Irgashev, R.A.; Postovsky Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
© Copyright 2015 Elsevier B.V., All rights reserved.

Cited by 16 documents

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