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

A direct sp 3 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 o...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-07, Vol.19 (28), p.625-6255
Main Authors: Rostoll-Berenguer, Jaume, Capella-Argente, Murta, Blay, Gonzalo, Pedro, José R, Vila, Carlos
Format: Article
Language:English
Subjects:
Amination
Amines
Benzoxazines
Chemical synthesis
Irradiation
Light irradiation
Photocatalysts
Quinoxaline
Quinoxalines
Radiation
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Summary:A direct sp 3 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. We describe a direct amination of cyclic amines with dialkyl azodicarboxylates accelerated by visible-light irradiation affording the corresponding products as versatile building blocks for divergent synthesis.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01157j