Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy
Author(s)
Willumstad, Thomas Paul; Boudreau, Paul D; Danheiser, Rick Lane
DownloadDanheiser 8-7 Revised Text[1].pdf (652.5Kb)
PUBLISHER_POLICY
Publisher Policy
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.
Terms of use
Metadata
Show full item recordAbstract
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.
Date issued
2015-08Department
Massachusetts Institute of Technology. Department of ChemistryJournal
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.
Version: Author's final manuscript
ISSN
0022-3263
1520-6904