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Synthesis 2018; 50(11): 2221-2230
DOI: 10.1055/s-0037-1609345
paper
© Georg Thieme Verlag Stuttgart · New York

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

Huy V. Huynh*
a   Department of Process Chemistry, Gilead Alberta ULC, 1021 Hayter Road NW, Edmonton, Alberta T6S 1A1, Canada
,
Selçuk Çalimsiz
a   Department of Process Chemistry, Gilead Alberta ULC, 1021 Hayter Road NW, Edmonton, Alberta T6S 1A1, Canada
,
Hilaire V. Kemami Wangun
b   Department of Analytical Chemistry, Gilead Alberta ULC, 1021 Hayter Road NW, Edmonton, Alberta T6S 1A1, Canada
,
Trevor J. Rainey
c   Department of Process Chemistry, Gilead Sciences, 333 Lakeside Drive, Foster City, CA 94404, USA
,
Teague M. McGinitie
b   Department of Analytical Chemistry, Gilead Alberta ULC, 1021 Hayter Road NW, Edmonton, Alberta T6S 1A1, Canada
,
Xiaoming Liao
d   Department of Process Development and Manufacturing, Pharmaron Beijing, Co. Ltd., 6 Tai-He Road, BDA, Beijing, 100176, P. R. of China   eMail: Huy.Huynh@gilead.com
,
Lizhi Yu
d   Department of Process Development and Manufacturing, Pharmaron Beijing, Co. Ltd., 6 Tai-He Road, BDA, Beijing, 100176, P. R. of China   eMail: Huy.Huynh@gilead.com
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Publikationsverlauf

Received: 15. Januar 2018

Accepted after revision: 18. Februar 2018

Publikationsdatum:
03. April 2018 (online)

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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.

Key words

quinoxalin-2-ones - 2-aminoanilines - α-ketimine esters - one-pot synthesis - transimination - regioselectivity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609345.
  • Supporting Information
 

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