Pd(PPh3)4/AgOAc-catalyzed one-pot synthesis of substituted 3,4-dihydronaphthalen-1(2H)-ones

被引：4

作者：

Liu, Hui ^{[1
]}

Yan, Peiyun ^{[1
]}

Li, Yan ^{[1
]}

Liu, Jinliang ^{[1
]}

Sun, Qian ^{[1
]}

Wang, Xingbin ^{[1
]}

Wang, Cunde ^{[1
]}

机构：

[1] Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou, Peoples R China

来源：

MONATSHEFTE FUR CHEMIE | 2012年 / 143卷 / 07期

关键词：

Alkynes; Carbocycles; Catalysis; Cycloadditions; One-pot synthesis; ADRENERGIC BLOCKING-AGENTS; DERIVATIVES; 3,4-DIHYDRO-1(2H)-NAPHTHALENONE; ANALOGS;

D O I：

10.1007/s00706-011-0681-5

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel and efficient one-pot synthesis of 3,4-dihydronaphthalen-1(2H)-ones by employing 2-iodocyclohex-2-enones, 1-alkynes, and a Pd[(C6H5)(3)P](4)/AgOAc catalytic system is described. The attractive features of this method, which enables the facile preparation of 3,4-dihydronaphthalen-1(2H)-one derivatives, are its very simple and straightforward procedure, mild reaction conditions, and good yields (65-87%).

引用

页码：1055 / 1059

页数：5

共 19 条

[1] Effects of 4,4-dimethyl-5,8-dihydroxynaphtalene-1-one and 4,4-dimethyl-5,8-dihydroxytetralone derivatives on tumor cell respiration [J].

Araya-Maturana, R ;

Delgado-Castro, T ;

Gárate, M ;

Ferreira, J ;

Pavani, M ;

Pessoa-Mahana, H ;

Cassels, BK .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (09) :3057-3060

[2] Synthesis and evaluation of dimeric 1,2,3,4-Tetrahydro-naphthalenylamine and Indan-1-ylamine derivatives with mast cell-stabilising and anti-allergic activity [J].

Barlow, James W. ;

Walsh, John J. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (01) :25-37

[3] Synthesis and evaluation of 4-amino-3,4-dihydro-2H-naphthalen-1-one derivatives as mast cell stabilising and anti-inflammatory compounds [J].

Barlow, James W. ;

Walsh, John J. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (12) :2891-2900

[4] O-Methylasparvenone, a nitrogen-free serotonin antagonist [J].

Bos, M ;

Canesso, R ;

Inoue-Ohga, N ;

Nakano, A ;

Takehana, Y ;

Sleight, AJ .

BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (12) :2165-2171

[5] SYNTHESIS AND OXIDATIVE ACTIVATION OF AN OXABICYCLO[7.2.1] ENEDIYNE [J].

BRANDSTETTER, T ;

MAIER, ME .

TETRAHEDRON, 1994, 50 (05) :1435-1448

[6] Bifunctional AgOAc-catalyzed asymmetric reactions [J].

Chen, Qing-An ;

Wang, Duo-Sheng ;

Zhou, Yong-Gui .

CHEMICAL COMMUNICATIONS, 2010, 46 (23) :4043-4051

[7] Practical and efficient Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by recyclable Pd(0)/C [J].

Felpin, FX .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8575-8578

[8] A comparative study on the inhibition of human and bacterial kynureninase by novel bicyclic kynurenine analogues [J].

Fitzgerald, DH ;

Muirhead, KM ;

Botting, NP .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (04) :983-989

[9] Palladium-Catalyzed Three-Component 1:2:1 Coupling of Aryl Iodides, Alkynes, and Alkenes to Produce 1,3,5-Hexatriene Derivatives [J].

Horiguchi, Hakaru ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (09) :1431-1436

[10] Dihydronaphthalenones from the endophytic fungus Botryosphaeria sp BCC 8200 [J].

Isaka, Masahiko ;

Yangchum, Arunrat ;

Rachtawee, Pranee ;

Khoyaiklang, Punsa ;

Boonyuen, Nattawut ;

Lumyong, Saisamorn .

PHYTOCHEMISTRY LETTERS, 2009, 2 (04) :207-210

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