Metal free TBHP-promoted intramolecular carbonylation of arenes via radical cross-dehydrogenative coupling: synthesis of indenoquinolinones, 4-azafluorenones and fluorenones

被引：35

作者：

Mishra, Kalpana ^{[1
]}

Pandey, Ashok Kumar ^{[2
]}

Singh, Jay Bahadur ^{[1
]}

Singh, Radhey M. ^{[1
]}

机构：

[1] Banaras Hindu Univ, Inst Sci, Ctr Adv Studies, Dept Chem, Varanasi 221005, Uttar Pradesh, India

[2] Indian Inst Technol Ropar, Dept Chem, Nangal Rd, Rupnagar 140001, Punjab, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 26期

关键词：

C-H ACTIVATION; AROMATIC-SUBSTITUTION BHAS; FACILE SYNTHESIS; BOND FORMATION; ANTIPROLIFERATIVE EVALUATION; EFFICIENT SYNTHESIS; ALDOXIME ETHERS; ARYL HALIDES; DERIVATIVES; ARYLATION;

D O I：

10.1039/c6ob00998k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free, TBHP-promoted economical route is developed via the sp(2) C-H bond functionalization strategy for the synthesis of indenoquinolinones, 4-azafluorenones and fluorenones. Reactions provided excellent yield of the products under mild conditions. We have successfully synthesized 11H-indeno [1,2-b]quinolin-11-one, an antibacterial agent, in excellent yields.

引用

页码：6328 / 6336

页数：9

共 18 条

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[14] Transition-Metal-Controlled Synthesis of 11H-Benzo[a]carbazoles and 6-Alkylidene-6H-isoindo[2,1-a]indoles via Sequential Intermolecular/Intramolecular Cross-Dehydrogenative Coupling from 2-Phenylindoles
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[15] 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
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[16] Di-tert-butyl peroxide (DTBP) promoted dehydrogenative coupling: an expedient and metal-free synthesis of oxindoles via intramolecular C(sp2)-H and C(sp3)-H bond activation
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[17] Metal-free new synthesis of 1,3-naphthoxazines via intramolecular cross dehydrogenative-coupling reaction of 1-(α-aminoalkyl)-2-naphthols using hypervalent iodine(III) reagent
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[18] tert-Butylhydroperoxide (TBHP) mediated oxidative cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with 4-hydroxycoumarins, 4-hydroxy-6-methyl-2pyrone and 2-hydroxy-1,4-naphthoquinone under metal-free conditions (vol 18, pg 6537, 2020)
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