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Org Lett. 2017 Aug 4;19(15):3994-3997. doi: 10.1021/acs.orglett.7b01701. Epub 2017 Jul 20.

A Modular Synthesis of 4-Aminoquinolines and [1,3] N-to-C Rearrangement to Quinolin-4-ylmethanesulfonamides.

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1
Department of Chemistry and Chemistry Institute of Functional Materials, Pusan National University , Busan 609-735, Korea.

Abstract

A copper-catalyzed regiocontrolled three-component reaction afforded diversified 4-aminoquinolines using nitriles, diaryliodoniums, and ynamides. 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 were newly developed. Finally, antimalarial CK-2-68 was successfully prepared.

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