Metal-Free Synthesis of 3,3-Disubstituted Oxoindoles by Iodine(III)-Catalyzed Bromocarbocyclizations

“I” did it: An iodine(III)‐mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles. This method is applicable to a variety of structurally different substrates, also with chemically sensitive groups, and gives access to the heterocycles in a regio‐ and ster...

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Published in:Chemistry : a European journal Vol. 18; no. 35; pp. 10834 - 10838
Main Authors: Fabry, David C., Stodulski, Maciej, Hoerner, Stefanie, Gulder, Tanja
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 27-08-2012
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Abstract “I” did it: An iodine(III)‐mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles. This method is applicable to a variety of structurally different substrates, also with chemically sensitive groups, and gives access to the heterocycles in a regio‐ and stereoselective fashion (see scheme). The indole‐2‐ones obtained can be converted easily into structurally complex target compounds, such as the alkaloid physostigmine.
AbstractList "I" did it: An iodine(III)-mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles. This method is applicable to a variety of structurally different substrates, also with chemically sensitive groups, and gives access to the heterocycles in a regio- and stereoselective fashion. The indole-2-ones obtained can be converted easily into structurally complex target compounds, such as the alkaloid physostigmine.
“I” did it: An iodine(III)‐mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles. This method is applicable to a variety of structurally different substrates, also with chemically sensitive groups, and gives access to the heterocycles in a regio‐ and stereoselective fashion (see scheme). The indole‐2‐ones obtained can be converted easily into structurally complex target compounds, such as the alkaloid physostigmine.
Author Fabry, David C.
Gulder, Tanja
Stodulski, Maciej
Hoerner, Stefanie
Author_xml – sequence: 1
  givenname: David C.
  surname: Fabry
  fullname: Fabry, David C.
  organization: Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52056 Aachen (Germany), Fax: (+49) 241-8092665
– sequence: 2
  givenname: Maciej
  surname: Stodulski
  fullname: Stodulski, Maciej
  organization: Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52056 Aachen (Germany), Fax: (+49) 241-8092665
– sequence: 3
  givenname: Stefanie
  surname: Hoerner
  fullname: Hoerner, Stefanie
  organization: Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52056 Aachen (Germany), Fax: (+49) 241-8092665
– sequence: 4
  givenname: Tanja
  surname: Gulder
  fullname: Gulder, Tanja
  email: tanja.gulder@rwth-aachen.de
  organization: Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52056 Aachen (Germany), Fax: (+49) 241-8092665
BackLink https://www.ncbi.nlm.nih.gov/pubmed/22786809$$D View this record in MEDLINE/PubMed
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Snippet “I” did it: An iodine(III)‐mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles. This method is applicable to a...
"I" did it: An iodine(III)-mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles. This method is applicable to a...
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pubmed
wiley
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StartPage 10834
SubjectTerms Acrylamides - chemistry
Alkaloids
Bromides - chemistry
bromocarbocyclization
Bromosuccinimide - chemistry
Catalysis
Chemistry
Cyclization
Halogenation
heterocycles
Indoles - chemical synthesis
Molecular Structure
natural products
organocatalysis
oxoindoles
Physostigmine
Physostigmine - chemical synthesis
Potassium Compounds - chemistry
Substrates
Synthesis
Title Metal-Free Synthesis of 3,3-Disubstituted Oxoindoles by Iodine(III)-Catalyzed Bromocarbocyclizations
URI https://api.istex.fr/ark:/67375/WNG-PH9GC5GQ-K/fulltext.pdf
https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.201201232
https://www.ncbi.nlm.nih.gov/pubmed/22786809
https://www.proquest.com/docview/1766761708
https://search.proquest.com/docview/1034200595
https://search.proquest.com/docview/1800490816
Volume 18
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