Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy
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Danheiser 8-7 Revised Text[1].pdf
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Author(s)
Willumstad, Thomas Paul
Boudreau, Paul D
Danheiser, Rick Lane
Date Issued
August 2015
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Citation
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.
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Author's final manuscript
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/acs.joc.5b01648
