Copper(I)-Catalyzed 3-Position Methylation of Coumarins by Using Di-tert-butyl Peroxide as the Methylation Reagents

被引：20

作者：

Zhuang, Huan ^{[1
]}

Zeng, Runsheng ^{[1
]}

Zou, Jianping ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Jiangsu, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2016年 / 34卷 / 04期

基金：

中国国家自然科学基金;

关键词：

CuCl; di-tert-butyl peroxide; methylation; coumarin; PALLADIUM-CATALYZED METHYLATION; C-H METHYLATION; BOND FUNCTIONALIZATION; COUPLING REACTION; CAFFEINE; INHIBITORS; DISCOVERY; OXINDOLES; ALKENES; SYSTEM;

D O I：

10.1002/cjoc.201500836

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The copper-catalyzed methylation of coumarin by using di-tert-butyl peroxide (DTBP) has been described. The reaction provides direct access to a wide range of 3-methylcoumarins in moderate to good yields. In this procedure, it is noteworthy that DTBP was employed not only as the oxidant, but also as the methyl source.

引用

页码：368 / 372

页数：5

共 49 条

[31]

PENNANEN SI, 1977, HETEROCYCLES, V6, P1181

[32]

Persson C. G., 1986, CLIN IMMUNOL, V78, P780

[33] 2,2'-BIFURYLIDENE-5,5'-DIONES, COUMARINS, 3A,7A-DIHYDRO-1H-INDEN-1-ONES, AND 5H-FURO[3,2-B]PYRAN-5-ONES FROM PROPYNE AND CARBON-MONOXIDE [J].

RAUTENSTRAUCH, V ;

MEGARD, P ;

GAMPER, B ;

BOURDIN, B ;

WALTHER, E ;

BERNARDINELLI, G .

HELVETICA CHIMICA ACTA, 1989, 72 (04) :811-824

[34] Antagonists for the Orphan G-Protein-Coupled Receptor GPR55 Based on a Coumarin Scaffold [J].

Rempel, Viktor ;

Volz, Nicole ;

Glaeser, Franziska ;

Nieger, Martin ;

Braese, Stefan ;

Mueller, Christa E. .

JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (11) :4798-4810

[35] Discovery of Coumarin-Dihydropyridine Hybrids as Bone Anabolic Agents [J].

Sashidhara, Koneni V. ;

Kumar, Manoj ;

Khedgikar, Vikram ;

Kushwaha, Priyanka ;

Modukuri, Ram K. ;

Kumar, Abdhesh ;

Gautam, Jyoti ;

Singh, Divya ;

Sridhar, Balasubramaniam ;

Trivedi, Ritu .

JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (01) :109-122

[36] Beyond Traditional Cross Couplings: The Scope of the Cross Dehydrogenative Coupling Reaction [J].

Scheuermann, Caroline J. .

CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (03) :436-451

[37] Profound Methyl Effects in Drug Discovery and a Call for New C-H Methylation Reactions [J].

Schoenherr, Heike ;

Cernak, Tim .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (47) :12256-12267

[38] THERMAL REARRANGEMENT OF ALPHA-(ARYLOXY)METHYLACRYLIC ACIDS - A FACILE SYNTHESIS OF 3-METHYLCOUMARINS [J].

SUNITHA, K ;

BALASUBRAMANIAN, KK ;

RAJAGOPALAN, K .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1530-1531

[39] Novel one-pot asymmetric cascade approach toward densely substituted enantioenriched α-methylene-γ-lactams [J].

Tan, Yu ;

Yang, Xiao-Di ;

Liu, Wen-Jie ;

Sun, Xing-Wen .

TETRAHEDRON LETTERS, 2014, 55 (44) :6105-6108

[40] Copper-Catalyzed N-Methylation of Amides and O-Methylation of Carboxylic Acids by Using Peroxides as the Methylating Reagents [J].

Xia, Qinqin ;

Liu, Xiaolong ;

Zhang, Yuejiao ;

Chen, Chao ;

Chen, Wanzhi .

ORGANIC LETTERS, 2013, 15 (13) :3326-3329

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