Synthesis 2019; 51(09): 2007-2013
DOI: 10.1055/s-0037-1612058
paper
© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of Onychines

Mao Arita
a  School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan   Email: nishiwaki.nagatoshi@kochi-tach.ac.jp
,
Soichi Yokoyama
a  School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan   Email: nishiwaki.nagatoshi@kochi-tach.ac.jp
b  Research Center for Material Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan
,
a  School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan   Email: nishiwaki.nagatoshi@kochi-tach.ac.jp
b  Research Center for Material Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan
c  Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan
,
a  School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan   Email: nishiwaki.nagatoshi@kochi-tach.ac.jp
b  Research Center for Material Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan
› Author Affiliations
Further Information

Publication History

Received: 07 November 2018

Accepted after revision: 06 December 2018

Publication Date:
19 February 2019 (eFirst)

Abstract

The FeCl3-mediated condensation of an α-phenylenamino ester and an enone proceeds efficiently to afford a 2-phenylnicotinate. The subsequent intramolecular Friedel–Crafts reaction yielded an ­onychine framework. Modifications at the 2-, 3-, and 8-positions of the onychine framework were easily achieved by altering the enamino esters­ and enones, which facilitated the discovery of potentially bioactive compounds.

Supporting Information

 
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