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

[1] TBHP-promoted and iodide-catalyzed synthesis of anhydrides via cross dehydrogenative coupling (CDC) of aldehydes
Singha, Raju
Ghosh, Munmun
Nuree, Yasin
Ray, Jayanta K.
TETRAHEDRON LETTERS, 2016, 57 (12) : 1325 - 1327
[2] TBHP Promoted Cross-Dehydrogenative coupling (CDC) Reaction: Metal/Additive-Free Synthesis of Chromone-Fused Quinolines
Singh, Jay B.
Mishra, Kalpana
Gupta, Tanu
Singh, Radhey M.
CHEMISTRYSELECT, 2017, 2 (03): : 1207 - 1210
[3] Scope of Successive C-H Functionalizations of the Methyl Group in 3-Picolines: Intramolecular Carbonylation of Arenes to the Metal-Free Synthesis of 4-Azafluorenones
Laha, Joydev K.
Jethava, Krupal P.
Patel, Sagarkumar
ORGANIC LETTERS, 2015, 17 (23) : 5890 - 5893
[4] Metal-free cross-dehydrogenative coupling of aryl aldehydes to give symmetrical carboxylic anhydrides promoted by the TBHP/nBu4PBr system
Adib, Mehdi
Pashazadeh, Rahim
Rajai-Daryasarei, Saideh
Mirzaei, Peiman
Gohari, Seyed Jamal Addin
TETRAHEDRON LETTERS, 2016, 57 (29) : 3071 - 3074
[5] Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone
Jourjine, Ilya A. P.
Zeisel, Lukas
Krauss, Juergen
Bracher, Franz
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 2668 - 2679
[6] TBHP/n-Bu4PBr-Promoted Oxidative Cross-Dehydrogenative Coupling of Aryl Methanols: A Facile Synthesis of Symmetrical Carboxylic Anhydride Derivatives
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SYNLETT, 2018, 29 (01) : 136 - 140
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Jourjine, Ilya A. P.
Zeisel, Lukas
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BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 170 - 172
[8] Synthesis of Polycyclic Amines through Mild Metal-Free Tandem Cross-Dehydrogenative Coupling/Intramolecular Hydroarylation of N-Aryltetrahydroisoquinolines and Crotonaldehyde
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Chen, Dian-Feng
Chen, Shu-Sen
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (03) : 468 - 473
[9] Metal-Free C-2-H Alkylation of Quinazolin-4-ones with Alkanes via Cross-Dehydrogenative Coupling
Mao, Shuai
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[10] Metal-Free Synthesis of -Aminophosphonates from Tertiary Amines and P(O)H Compounds via a Cross-Dehydrogenative Coupling Reaction
Lin, Binzhou
Lu, Guozhang
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Cui, Yiqun
Liu, Yan
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SYNLETT, 2018, 29 (20) : 2697 - 2700

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