Issue 28, 2021
From the journal:

Organic & Biomolecular Chemistry

Visible-light-accelerated amination of quinoxalin-2-ones and benzo[1,4]oxazin-2-ones with dialkyl azodicarboxylates under metal and photocatalyst-free conditions†

Jaume Rostoll-Berenguer,a   Murta Capella-Argente,a   Gonzalo Blay, ORCID logo a   José R. Pedro ORCID logo *a  and  Carlos Vila ORCID logo *a  

* Corresponding authors

a Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València, Spain
E-mail: jose.r.pedro@uv.es, carlos.vila@uv.es

Abstract

A direct sp3 C–H amination of cyclic amines (dihydroquinoxalinones and dihydrobenzoxazinones) with dialkyl azo dicarboxylates accelerated by visible-light irradiation under metal and photocatalyst-free conditions is described. This protocol features very mild reaction conditions for the synthesis of aminal quinoxaline and benzoxazine derivatives with good to high yields (up to 99%). These aminal derivatives respresent versatile building blocks for the divergent synthesis of quinoxalin-2-one derivatives.

Graphical abstract: Visible-light-accelerated amination of quinoxalin-2-ones and benzo[1,4]oxazin-2-ones with dialkyl azodicarboxylates under metal and photocatalyst-free conditions

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Article information

DOI
https://doi.org/10.1039/D1OB01157J
Article type
Paper
Submitted
15 Jun 2021
Accepted
01 Jul 2021
First published
02 Jul 2021

Org. Biomol. Chem., 2021,19, 6250-6255

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Visible-light-accelerated amination of quinoxalin-2-ones and benzo[1,4]oxazin-2-ones with dialkyl azodicarboxylates under metal and photocatalyst-free conditions

J. Rostoll-Berenguer, M. Capella-Argente, G. Blay, J. R. Pedro and C. Vila, Org. Biomol. Chem., 2021, 19, 6250 DOI: 10.1039/D1OB01157J

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