tert-Butylhydroperoxide (TBHP) mediated oxidative cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with 4-hydroxycoumarins, 4-hydroxy-6-methyl-2-pyrone and 2-hydroxy-1,4-naphthoquinone under metal-free conditions

We report an efficient and atom-economical method of C-3 functionalization of quinoxalin-2(1H)-ones with 4-hydroxycoumarins, 4-hydroxy-6-methyl-2-pyrone, and 2-hydroxy-1,4-naphthoquinoneviathe free radical cross-coupling pathway under metal-free conditions.tert-Butylhydroperoxide (TBHP) smoothly pro...

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Published inOrganic & biomolecular chemistry Vol. 18; no. 33; pp. 6537 - 6548
Main Authors Sharma, Suraj, Dutta, Nibedita Baruah, Bhuyan, Mayurakhi, Das, Babulal, Baishya, Gakul
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 26.08.2020
Royal Society of Chemistry
Subjects
Butylated hydroxytoluene
Catalysts
Chemistry
Chemistry, Organic
Column chromatography
Cross coupling
Crystallography
Dehydrogenation
Free radicals
NMR
Nuclear magnetic resonance
Physical Sciences
Reagents
Science & Technology
DECARBOXYLATIVE ACYLATION
DESIGN
IN-VITRO ANTIBACTERIAL
C-3 ARYLATION
QUINOXALIN-2(H)-ONES
QUINOXALINONES
HIV-1 INTEGRASE INHIBITION
ACETYLCHOLINESTERASE INHIBITORS
DERIVATIVES
PHOTOCATALYST
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Summary:We report an efficient and atom-economical method of C-3 functionalization of quinoxalin-2(1H)-ones with 4-hydroxycoumarins, 4-hydroxy-6-methyl-2-pyrone, and 2-hydroxy-1,4-naphthoquinoneviathe free radical cross-coupling pathway under metal-free conditions.tert-Butylhydroperoxide (TBHP) smoothly promotes the reaction furnishing the cross-dehydrogenative coupling (CDC) products in very good to excellent yields. The protocol neither uses any toxic reagents nor metal catalysts to carry out the reaction, and all the products have been obtained without column chromatography purification. Different radical trapping experiments with 2,2,6,6-tetramethylpiperidine-1-oxyl, butylated hydroxytoluene, and diphenyl ethylene confirm the involvement of radicals.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01304h