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 |
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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. |
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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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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 |
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