Thiazolo[5,4- <i>f</i> ]quinoxalines, Oxazolo[5,4- <i>f</i> ]quinoxalines and Pyrazino[ <i>b,e</i> ]isatins: Synthesis from 6-Aminoquinoxalines and Properties - Université de Rennes Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2021

Thiazolo[5,4- f ]quinoxalines, Oxazolo[5,4- f ]quinoxalines and Pyrazino[ b,e ]isatins: Synthesis from 6-Aminoquinoxalines and Properties

William Erb
Olivier Mongin
Laurent Picot
Valérie Thiéry
Florence Mongin

Abstract

The regioselective iodination of different 2-mono-, 3-mono- and 2,3-disubstituted 6-aminoquinoxalines, which takes place at their 5-position, was rationalized on the basis of Hückel theory calculations. Oxazolo- and thiazolo[5,4-f]quinoxaline analogues of reported disease-related protein kinases inhibitors were synthesized from the obtained 6-amino-5-iodoquinoxalines by using as key step copper-catalyzed azole ring formation. Pyrazino[b,e]isatins were obtained, for the first time, from the same substrates by recourse to Sonogashira coupling, alkyne hydration, and oxidative cyclization. The absorption and emission properties of the most promising compounds were recorded. In addition, most of the synthesized polycycles were evaluated as protein kinase inhibitors and for their antiproliferative activity towards cancer cells.
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Dates and versions

hal-03269555 , version 1 (30-06-2021)

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Frédéric Lassagne, Joshua M. Sims, William Erb, Olivier Mongin, Nicolas Richy, et al.. Thiazolo[5,4- f ]quinoxalines, Oxazolo[5,4- f ]quinoxalines and Pyrazino[ b,e ]isatins: Synthesis from 6-Aminoquinoxalines and Properties. European Journal of Organic Chemistry, 2021, 2021 (19), pp.2756-2763. ⟨10.1002/ejoc.202100362⟩. ⟨hal-03269555⟩
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