Ytterbium triflate-catalyzed conjugate addition of β-ketoesters to activated 1,4-naphthoquinones

被引：36

作者：

Mudiganti, Naga Venkata Sastry ^{[1
]}

Claessens, Sven ^{[1
]}

De Kimpe, Norbert ^{[1
]}

机构：

[1] Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

来源：

TETRAHEDRON | 2009年 / 65卷 / 08期

关键词：

FREE-RADICAL REACTION; CYTOTOXICITY EVALUATION; DICARBONYL COMPOUNDS; PYRIDINIUM YLIDES; QUINONES; DERIVATIVES; 2-AMINO-1,4-NAPHTHOQUINONES; ALKYLATION;

D O I：

10.1016/j.tet.2008.12.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient procedure for the conjugate addition of various beta-ketoesters to activated 1,4-naphthoquinones using a catalytic amount of Yb(OTf)(3) was developed. The tri-, tetra-, and pentacyclic adducts were obtained in very good to excellent yield. Cyclic beta-ketoesters added smoothly to activated quinones when compared to their acyclic counterparts. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1716 / 1723

页数：8

共 27 条

[1] ADDUCTS FROM QUINONES AND DIAZOALKANES .10. 2-DIAZOPROPANE AND 2-METHYL-1,4-NAPHTHOQUINONE - STRUCTURES AND CONFORMATIONS OF NOVEL VINYLIC QUINONES AND EPOXIDES
ALDERSLEY, MF
DEAN, FM
MANN, BE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (12): : 2217 - 2222
[2] ALKYLATION OF QUINONES BY CARBANIONS - USE OF PYRIDINIUM YLIDES TO INSERT PHENACYL, ACETONYL AND RELATED GROUPS
ALDERSLEY, MF
DEAN, FM
NAYYIRMAZHIR, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08): : 1753 - 1757
[3] DERIVATIVES OF NAPHTHO[2,3-C]PYRAN-5,10-DIONE - A SIMPLE SYNTHESIS AND A NOTE OF THEIR CHROMOGENIC PROPERTIES
ALDERSLEY, MF
DEAN, FM
HAMZAH, AS
[J]. TETRAHEDRON LETTERS, 1986, 27 (02) : 255 - 258
[4] PYRIDINIUM YLIDES IN SYNTHESES OF NAPHTHOPYRANDIONES AND IN REGIOSELECTIVE SYNTHESES OF ACYLATED ANTHRAQUINONES RELATED TO FUNGAL AND BACTERIAL METABOLITES
ALDERSLEY, MF
CHISHTI, SH
DEAN, FM
DOUGLAS, ME
ENNIS, DS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (08): : 2163 - 2174
[5] MANGANESE(III) ACETATE INITIATED OXIDATIVE FREE-RADICAL REACTION BETWEEN 1,4-NAPHTHOQUINONE AND ALPHA-BENZYLMALONATES
CHUANG, CP
WANG, SF
[J]. TETRAHEDRON LETTERS, 1994, 35 (25) : 4365 - 4366
[6] Manganese(III) acetate initiated oxidative free radical reaction between 1,4-naphthoquinones and α-alkylmalonates
Chuang, CP
Wang, SF
[J]. TETRAHEDRON, 1998, 54 (34) : 10043 - 10052
[7] Manganese(III) acetate initiated oxidative free radical reaction between 1-anilino-1,4-naphthoquinones and diethyl malonate
Chuang, CP
Wang, SF
[J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1997, 44 (03) : 271 - 277
[8] A mild and efficient one-step synthesis of quinolines
De, SK
Gibbs, RA
[J]. TETRAHEDRON LETTERS, 2005, 46 (10) : 1647 - 1649
[9] FINLEY KT, 1988, QUINONES SYNTHON 1, V2, P654
[10] GORELIK MV, 1985, ZH VSES KHIM OVA+, V30, P576

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