Microwave assisted regioselective halogenation of benzo[ b ][1,4]oxazin-2-ones via sp 2 C-H functionalization

A microwave assisted, palladium-catalyzed regioselective halogenation of 3-phenyl-2 -benzo[ ][1,4]oxazin-2-ones has been demonstrated using inexpensive and readily available -halosuccinimide. The reaction utilizes the nitrogen atom present in the heterocyclic ring as the directing group to afford re...

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Bibliographic Details
Published in:RSC advances 2023-01, Vol.13 (4), p.2365-2371
Main Authors: Kumar, Sandeep, Prince, Gupta, Mohit, Lalji, Ram Sunil Kumar, Singh, Brajendra K
Format: Article
Language:English
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Summary:A microwave assisted, palladium-catalyzed regioselective halogenation of 3-phenyl-2 -benzo[ ][1,4]oxazin-2-ones has been demonstrated using inexpensive and readily available -halosuccinimide. The reaction utilizes the nitrogen atom present in the heterocyclic ring as the directing group to afford regioselective halogenated products in good to moderate yields. The established protocol provides wide substrate scope, high functional group tolerance, and high atom and step economy. The reaction proved to be cost-effective and time-saving as it required only a few minutes for completion and is amenable to gram scale. The halogen atoms present in synthesized products provide further scope for post-functionalization. Several post-functionalized products have also been synthesised to demonstrate the high utility of the reaction in the field of drug discovery and late-stage functionalization.
ISSN:2046-2069
2046-2069
DOI:10.1039/D2RA07259A