An Aniline-Mediated Regioselective Synthesis of Quinoxalin-2-ones via the Condensation of α-Ketimine Esters with 2-Aminoanilines

Author:

Huynh Huy1,Çalimsiz Selçuk1,Wangun Hilaire2,Rainey Trevor3,McGinitie Teague2,Liao Xiaoming4,Yu Lizhi4

Affiliation:

1. Department of Process Chemistry

2. Department of Analytical Chemistry

3. Department of Process Chemistry, Gilead Sciences

4. Department of Process Development and Manufacturing, Pharmaron Beijing, Co. Ltd.

Abstract

A highly regioselective method for the condensation of α-ketimine esters with 2-aminoanilines for the construction of quinoxalin-2-one derivatives is described. The substrate scope with 2-aminoaniline derivatives and different α-keto esters is explored with yields ranging from 44 to 90% and typical isolated regioselectivities between 6.4 to >25:1.

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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