Facile Synthesis of Onychines

Mao Arita; Soichi Yokoyama; Haruyasu Asahara; Nagatoshi Nishiwaki

doi:10.1055/s-0037-1612058

Synthesis, Table of Contents

Synthesis 2019; 51(09): 2007-2013
DOI: 10.1055/s-0037-1612058

paper

Facile Synthesis of Onychines

Mao Arita

^aSchool of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan Email: nishiwaki.nagatoshi@kochi-tach.ac.jp

,

Soichi Yokoyama

^aSchool of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan Email: nishiwaki.nagatoshi@kochi-tach.ac.jp

^bResearch Center for Material Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan

,

Haruyasu Asahara *

^aSchool of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan Email: nishiwaki.nagatoshi@kochi-tach.ac.jp

^bResearch Center for Material Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan

^cDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan

,

Nagatoshi Nishiwaki *

^aSchool of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan Email: nishiwaki.nagatoshi@kochi-tach.ac.jp

^bResearch Center for Material Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan

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Abstract

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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.

Key words

onychine - polysubstituted nicotinates - iron(III) chloride - intramolecular Friedel–Crafts reaction - enone

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References

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