A Modular Synthesis of 4-Aminoquinolines and [1,3] N-to-C Rearrangement to Quinolin-4-ylmethanesulfonamides
Kyung Hwan Oh, Jin Gyeong Kim and Jin Kyoon Park*
*Department of Chemistry and Chemistry Institute of
Functional Materials, Pusan National University, Busan 609-735, Korea, Email:
pjkyoon
pusan.ac.kr
K. H. Oh, J. G. Kim, J. K. Park, Org. Lett., 2017, 19, 3994-3997.
DOI: 10.1021/acs.orglett.7b01701
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Abstract
A copper-catalyzed regiocontrolled three-component reaction of nitriles, diaryliodoniums, and ynamides provides diversified 4-aminoquinolines. The C7-substituted regioisomers were formed regioselectively when meta-substituted phenyliodonium salts were used. [1,3] N-to-C rearrangement of the products to quinolin-4-ylmethanesulfonamides and simultaneous deprotection of benzyl and sulfonamide group are also reported.
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Key Words
quinolines, multicomponent reactions
ID: J54-Y2017
