Benzannulation via the Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles
A two-stage “tandem strategy” for the synthesis of indoles with a high level of substitution on the six-membered ring is described. Benzannulation based on the reaction of cyclobutenones with ynamides proceeds via a cascade of four pericyclic reactions to produce multiply substituted aniline derivat...
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| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2014
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| Online Access: | http://hdl.handle.net/1721.1/88725 https://orcid.org/0000-0002-9812-206X https://orcid.org/0000-0001-5002-2230 |
| _version_ | 1811096742451478528 |
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| author | Lam, Tin Yiu Wang, Yu-Pu Danheiser, Rick Lane |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Lam, Tin Yiu Wang, Yu-Pu Danheiser, Rick Lane |
| author_sort | Lam, Tin Yiu |
| collection | MIT |
| description | A two-stage “tandem strategy” for the synthesis of indoles with a high level of substitution on the six-membered ring is described. Benzannulation based on the reaction of cyclobutenones with ynamides proceeds via a cascade of four pericyclic reactions to produce multiply substituted aniline derivatives in which the position ortho to the nitrogen can bear a wide range of functionalized substituents. In the second stage of the tandem strategy, highly substituted indoles are generated via acid-, base-, and palladium-catalyzed cyclization and annulation processes. |
| first_indexed | 2024-09-23T16:48:20Z |
| format | Article |
| id | mit-1721.1/88725 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T16:48:20Z |
| publishDate | 2014 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/887252022-10-03T08:25:53Z Benzannulation via the Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles Lam, Tin Yiu Wang, Yu-Pu Danheiser, Rick Lane Massachusetts Institute of Technology. Department of Chemistry Danheiser, Rick Lane Lam, Tin Yiu Wang, Yu-Pu Danheiser, Rick Lane A two-stage “tandem strategy” for the synthesis of indoles with a high level of substitution on the six-membered ring is described. Benzannulation based on the reaction of cyclobutenones with ynamides proceeds via a cascade of four pericyclic reactions to produce multiply substituted aniline derivatives in which the position ortho to the nitrogen can bear a wide range of functionalized substituents. In the second stage of the tandem strategy, highly substituted indoles are generated via acid-, base-, and palladium-catalyzed cyclization and annulation processes. National Institutes of Health (U.S.) (Grant GM28273) National Science Foundation (U.S.) (Grant CHE-1111567) Merck Research Laboratories Boehringer Ingelheim Pharmaceuticals Eli Lilly and Company (Graduate Fellowship) Massachusetts Institute of Technology. Dept. of Chemistry (C.P. Chu and Y. Lai Fellowship Fund) 2014-08-15T17:01:41Z 2014-08-15T17:01:41Z 2013-09 Article http://purl.org/eprint/type/JournalArticle 0022-3263 1520-6904 http://hdl.handle.net/1721.1/88725 Lam, Tin Yiu, Yu-Pu Wang, and Rick L. Danheiser. “Benzannulation via the Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles.” The Journal of Organic Chemistry 78, no. 18 (September 20, 2013): 9396–9414. https://orcid.org/0000-0002-9812-206X https://orcid.org/0000-0001-5002-2230 en_US http://dx.doi.org/10.1021/jo401635c Journal of Organic Chemistry Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) Prof. Danheiser via Erja Kajosalo |
| spellingShingle | Lam, Tin Yiu Wang, Yu-Pu Danheiser, Rick Lane Benzannulation via the Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles |
| title | Benzannulation via the Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles |
| title_full | Benzannulation via the Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles |
| title_fullStr | Benzannulation via the Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles |
| title_full_unstemmed | Benzannulation via the Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles |
| title_short | Benzannulation via the Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles |
| title_sort | benzannulation via the reaction of ynamides and vinylketenes application to the synthesis of highly substituted indoles |
| url | http://hdl.handle.net/1721.1/88725 https://orcid.org/0000-0002-9812-206X https://orcid.org/0000-0001-5002-2230 |
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