Radical-mediated remote migration of quinoxalinones

Disclosed herein is the first example of radical-mediated remote migration of quinoxalinones. The quinoxalinonyl-functionalization of alkenes employs the quinoxalinone-substituted tertiary bishomoallylic alcohols as substrates, proceeds through intramolecular 1,4-quinoxalinone migration, and gives r...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2023-04, Vol.59 (3), p.4499-452
Main Authors: Chang, Chenyang, Zhang, Qi, Wu, Xinxin, Zhu, Chen
Format: Article
Language:English
Subjects:
Alcohols
Functional groups
Ketones
Substitutes
Substrates
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Summary:Disclosed herein is the first example of radical-mediated remote migration of quinoxalinones. The quinoxalinonyl-functionalization of alkenes employs the quinoxalinone-substituted tertiary bishomoallylic alcohols as substrates, proceeds through intramolecular 1,4-quinoxalinone migration, and gives rise to complex γ-quinoxalinone-substituted aliphatic ketones. A set of external radicals is compatible with this method. The protocol features broad tolerance of functional groups, good adaptability to various external radicals and high product diversity, and opens a new door for the synthesis of quinoxalinone derivatives. Described herein is the first example of radical-mediated remote quinoxalinone migration.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc06887g