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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: pjkyoonpusan.ac.kr

K. H. Oh, J. G. Kim, J. K. Park, Org. Lett., 2017, 19, 3994-3997.

DOI: 10.1021/acs.orglett.7b01701 (free Supporting Information)


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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