Tandem Blaise-Nenitzescu reaction: one-pot synthesis of 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones from nitriles

被引：23

作者：

Chun, Yu Sung ^{[2
]}

Ryu, Ka Yeon ^{[2
]}

Kim, Ju Hyun ^{[2
]}

Shin, Hyunik ^{[1
]}

Lee, Sang-gi ^{[2
]}

机构：

[1] LG Life Sci Ltd R&D, Chem Dev Div, Taejon 305380, South Korea

[2] Ewha Womans Univ, Dept Chem & Nano Sci BK21, Seoul 120750, South Korea

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 05期

关键词：

ACYLATION;

D O I：

10.1039/c0ob01024c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In contrast to the reaction of benzoquinones with beta-enaminoesters providing indoles (Nenitzescu reaction), the tandem one-pot reaction of the Blaise reaction intermediate, zinc bromide complex of beta-enaminoesters, with benzoquinone affords 5-hydroxy-alpha-(aminomethylene)benzofuran-2(3H)-ones in good to excellent yields (tandem Blaise-Nenitzescu reaction).

引用

页码：1317 / 1319

页数：3

共 17 条

[1]

Allen G.R., 1973, Org. React, V20, P337

[2] Indolequinone antitumor agents:: Correlation between quinone structure, rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase, and in vitro cytotoxicity [J].

Beall, HD ;

Winski, S ;

Swann, E ;

Hudnott, AR ;

Cotterill, AS ;

O'Sullivan, N ;

Green, SJ ;

Bien, R ;

Siegel, D ;

Ross, D ;

Moody, CJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (24) :4755-4766

[3] Synthesis and pharmacology of benzoxazines as highly selective antagonists at M4 muscarinic receptors [J].

Böhme, TM ;

Augelli-Szafran, CE ;

Hallak, H ;

Pugsley, T ;

Serpa, K ;

Schwarz, RD .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (14) :3094-3102

[4] The first chemoselective tandem acylation of the Blaise reaction intermediate: a novel method for the synthesis of α-acyl-β-enamino esters, key intermediate for pyrazoles [J].

Chun, Yu Sung ;

Lee, Ki Kon ;

Ko, Young Ok ;

Shin, Hyunik ;

Lee, Sang-gi .

CHEMICAL COMMUNICATIONS, 2008, (41) :5098-5100

[5] One-Pot Synthesis of 2-Pyridones via Chemo- and Regioselective Tandem Blaise Reaction of Nitriles with Propiolates [J].

Chun, Yu Sung ;

Ryu, Ka Yeon ;

Ko, Young Ok ;

Hong, Joo Yeon ;

Hong, Jongki ;

Shin, Hyunik ;

Lee, Sang-gi .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) :7556-7558

[6] Tandem Blaise-Alkenylation with Unactivated Alkynes: One-Pot Synthesis of α-Vinylated β-Enaminoesters from Nitriles [J].

Chun, Yu Sung ;

Ko, Young Ok ;

Shin, Hyunik ;

Lee, Sang-gi .

ORGANIC LETTERS, 2009, 11 (15) :3414-3417

[7] From Oblivion into the Limelight: Iron (Domino) Catalysis [J].

Fuerstner, Alois .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (08) :1364-1367

[8]

HO TL, 1992, TENDEM ORGANIC REACT

[9] An effective and general method for the highly regioselective synthesis of 1-phenylpyrazoles from β-enaminoketoesters, tandem Blaise-acylation adducts [J].

Ko, Young Ok ;

Chun, Yu Sung ;

Park, Cho-Long ;

Kim, Youngmee ;

Shin, Hyunik ;

Ahn, Sungho ;

Hong, Jongki ;

Lee, Sang-gi .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (06) :1132-1136

[10]

Kurti L., 2005, STRATEGIC APPL NAMED, P312

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