Copper(II) bromide-catalyzed intramolecular decarboxylative functionalization to form a C(sp3)-O bond for the synthesis of furo[3,2-c]-coumarins

被引：19

作者：

Zhang, W. L. ^{[1
,2
]}

Yue, S. N. ^{[1
,2
]}

Shen, Y. M. ^{[3
]}

Hu, H. Y. ^{[4
]}

Meng, Q-H. ^{[1
,2
]}

Wu, H. ^{[1
,2
]}

Liu, Y. ^{[1
,2
]}

机构：

[1] Jiangsu Normal Univ, Jiangsu Key Lab Green Synth Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China

[2] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Jiangsu, Peoples R China

[3] Shaoxing Univ, Sch Chem & Chem Engn, Shaoxing, Zhejiang, Peoples R China

[4] Huaiyin Normal Univ, Jiangsu Key Lab Chem Low Dimens Mat, Sch Chem & Chem Engn, Huaian 223300, Jiangsu, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 12期

基金：

中国国家自然科学基金;

关键词：

CARBON TRIPLE BOND; ONE-POT SYNTHESIS; MOLECULAR-OXYGEN; NEO-TANSHINLACTONE; ANTITUMOR AGENTS; DERIVATIVES; AMINATION; CASCADE; CYCLOADDITION; COUMARIN;

D O I：

10.1039/c4ob02490g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and eco-friendly copper(II) bromide-catalyzed intramolecular decarboxylative functionalization to form a C(sp(3))-O bond for the synthesis of furo[3,2-c]coumarins has been developed. In this reaction, a copper(II) bromide-catalyzed intramolecular decarboxylative functionalization of a-carbonyl is successfully realized to generate an a-bromo carbonyl compound as a key intermediate.

引用

页码：3602 / 3609

页数：8

共 51 条

[1] Regio and diastereoselective synthesis of functionalized 2,3-dihydrofuro[3,2-c]coumarins via a one-pot three-component reaction [J].

Altieri, Elisa ;

Cordaro, Massimiliano ;

Grassi, Giovanni ;

Risitano, Francesco ;

Scala, Angela .

TETRAHEDRON, 2010, 66 (49) :9493-9496

[2]

[Anonymous], 1982, NATURAL COUMARINS OC, DOI DOI 10.1016/0160-9327(83)90060-1

[3]

[Anonymous], ADV ORG SYNTH

[4] PSEUDOPTEROLIDE, AN IRREGULAR DITERPENOID WITH UNUSUAL CYTO-TOXIC PROPERTIES FROM THE CARIBBEAN SEA WHIP PSEUDOPTEROGORGIA-ACEROSA (PALLAS) (GORGONACEA) [J].

BANDURRAGA, MM ;

FENICAL, W ;

DONOVAN, SF ;

CLARDY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (23) :6463-6465

[5]

Boland GM, 1998, NAT PROD REP, V15, P241

[6] Two efficient cascade reactions to synthesize substituted furocoumarins [J].

Cheng, Gang ;

Hu, Youhong .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4732-4735

[7] One-pot synthesis of furocoumarins through cascade addition-cyclization-oxidation [J].

Cheng, Gang ;

Hu, Youhong .

CHEMICAL COMMUNICATIONS, 2007, (31) :3285-3287

[8] PHOTOPHERESIS - PRESENT AND FUTURE ASPECTS [J].

EDELSON, RL .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 1991, 10 (1-2) :165-171

[9] Simple Catalytic Mechanism for the Direct Coupling of α-Carbonyls with Functionalized Amines: A One-Step Synthesis of Plavix [J].

Evans, Ryan W. ;

Zbieg, Jason R. ;

Zhu, Shaolin ;

Li, Wei ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16074-16077

[10] One-pot synthesis of benzo[b]furan and indole inhibitors of tubulin polymerization [J].

Flynn, BL ;

Hamel, E ;

Jung, MK .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (12) :2670-2673

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