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

被引：15

作者：

Sharma, Suraj ^{[1
,2
]}

Dutta, Nibedita Baruah ^{[1
,2
,3
]}

Bhuyan, Mayurakhi ^{[1
,2
]}

Das, Babulal ^{[4
]}

Baishya, Gakul ^{[1
,2
]}

机构：

[1] CSIR North East Inst Sci & Technol, Chem Sci & Technol Div, Jorhat 785006, Assam, India

[2] Acad Sci & Innovat Res, Ghaziabad 201002, Uttar Pradesh, India

[3] Rain Forest Res Inst, Jorhat 785001, Assam, India

[4] Indian Inst Technol Guwahati, Dept Chem, Gauhati, Assam, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 33期

关键词：

HIV-1 INTEGRASE INHIBITION; IN-VITRO ANTIBACTERIAL; ACETYLCHOLINESTERASE INHIBITORS; DECARBOXYLATIVE ACYLATION; C-3; ARYLATION; DESIGN; QUINOXALIN-2(H)-ONES; QUINOXALINONES; PHOTOCATALYST; DERIVATIVES;

D O I：

10.1039/d0ob01304h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：6537 / 6548

页数：12

共 101 条

[1]

[Anonymous], 2005, BIOTECHNOL BIOTEC EQ

[2] Convenient synthetic method for 3-(3-substituted indol-2-yl)quinoxalin-2-ones as VEGF inhibitor [J].