Copper-catalyzed synthesis of aminoquinolines from β-(2-aminophenyl)-α,β-ynones using DMF as dual synthon.

Chem Commun (Camb)

Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, Republic of China. and Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 80708, Taiwan, Republic of China and Drug Development and Value Creation Research Centre, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, Republic of China.

Published: June 2020

A new and efficient method has been developed for the synthesis of 4-aminoquinoline through aerobic Cu(i)-catalyzed cyclization of β-(2-aminophenyl)-α,β-ynones. Under the optimized conditions, DMF could serve as a methine source to introduce C2 carbon and a nitrogen source to incorporate amino functionality in the 4th position. Mechanistic studies using 13C- and DMF-d7 revealed that the methine group was derived from a methyl substituent.

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http://dx.doi.org/10.1039/d0cc03033cDOI Listing

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