Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy
A two-stage “tandem strategy” for the regiocontrolled synthesis of very highly substituted quinolines is described. Benzannulation based on the reaction of cyclobutenones or diazo ketones with N-propargyl-substituted ynamides proceeds via a cascade of several pericyclic reactions to generate multipl...
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| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2017
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| Online Access: | http://hdl.handle.net/1721.1/108246 https://orcid.org/0000-0002-9812-206X |
| _version_ | 1826210493864345600 |
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| author | Willumstad, Thomas Paul Boudreau, Paul D Danheiser, Rick Lane |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Willumstad, Thomas Paul Boudreau, Paul D Danheiser, Rick Lane |
| author_sort | Willumstad, Thomas Paul |
| collection | MIT |
| description | A two-stage “tandem strategy” for the regiocontrolled synthesis of very highly substituted quinolines is described. Benzannulation based on the reaction of cyclobutenones or diazo ketones with N-propargyl-substituted ynamides proceeds via a cascade of several pericyclic reactions to generate multiply substituted aniline derivatives. In the second stage of the tandem strategy, triflate derivatives of the phenolic benzannulation products undergo Larock cyclization upon exposure to iodine to form products that are further elaborated by methods such as palladium-catalyzed coupling to generate quinolines that can be substituted at every position of the bicyclic system. |
| first_indexed | 2024-09-23T14:50:27Z |
| format | Article |
| id | mit-1721.1/108246 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T14:50:27Z |
| publishDate | 2017 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1082462022-09-29T10:55:33Z Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy Willumstad, Thomas Paul Boudreau, Paul D Danheiser, Rick Lane Massachusetts Institute of Technology. Department of Chemistry Danheiser, Rick L. Willumstad, Thomas Paul Boudreau, Paul D Danheiser, Rick Lane A two-stage “tandem strategy” for the regiocontrolled synthesis of very highly substituted quinolines is described. Benzannulation based on the reaction of cyclobutenones or diazo ketones with N-propargyl-substituted ynamides proceeds via a cascade of several pericyclic reactions to generate multiply substituted aniline derivatives. In the second stage of the tandem strategy, triflate derivatives of the phenolic benzannulation products undergo Larock cyclization upon exposure to iodine to form products that are further elaborated by methods such as palladium-catalyzed coupling to generate quinolines that can be substituted at every position of the bicyclic system. National Science Foundation (U.S.) (CHE-1111567) National Institutes of Health (U.S.) (GM 28273) Merck Research Laboratories Boehringer Ingelheim Pharmaceuticals AstraZeneca (Firm) (Graduate Fellowship) David A. Johnson, Merck, and George Büchi Summer fellowships. 2017-04-19T14:43:53Z 2017-04-19T14:43:53Z 2015-08 2015-07 Article http://purl.org/eprint/type/JournalArticle 0022-3263 1520-6904 http://hdl.handle.net/1721.1/108246 Willumstad, Thomas P., Paul D. Boudreau, and Rick L. Danheiser. “Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy.” J. Org. Chem. 80, no. 23 (December 4, 2015): 11794–11805. doi:10.1021/acs.joc.5b01648. ©2015. https://orcid.org/0000-0002-9812-206X en_US http://dx.doi.org/10.1021/acs.joc.5b01648 The 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 | Willumstad, Thomas Paul Boudreau, Paul D Danheiser, Rick Lane Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy |
| title | Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy |
| title_full | Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy |
| title_fullStr | Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy |
| title_full_unstemmed | Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy |
| title_short | Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy |
| title_sort | synthesis of highly substituted quinolines via a tandem ynamide benzannulation iodocyclization strategy |
| url | http://hdl.handle.net/1721.1/108246 https://orcid.org/0000-0002-9812-206X |
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