Microwave-assisted solid-phase Dotz benzannulation reaction: a facile synthesis of 2,3-disubstituted-1,4-naphthoquinones

被引:14
作者
Shanmugasundaram, M [1 ]
Garcia-Martinez, I [1 ]
Li, QY [1 ]
Estrada, A [1 ]
Martinez, NE [1 ]
Martinez, LE [1 ]
机构
[1] Univ Texas, Dept Chem, El Paso, TX 79968 USA
基金
美国国家卫生研究院;
关键词
solid-phase synthesis; microwave; Dotz reaction; 1,4-naphthoquinones; Fischer carbenes;
D O I
10.1016/j.tetlet.2005.08.158
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A microwave-assisted solid-supported Dotz benzannulation of chromium carbene complexes with various alkynes has been developed. The oxidative cleavage of the resulting resin-bound 1,4-naphthols affords 2,3-disubstituted-1,4-naphthoquinone derivatives in good to moderate yields with high purities. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7545 / 7548
页数:4
相关论文
共 39 条
[1]   Transition-metal-mediated reactions in combinatorial synthesis [J].
Andres, CJ ;
Whitehouse, DL ;
Deshpande, MS .
CURRENT OPINION IN CHEMICAL BIOLOGY, 1998, 2 (03) :353-362
[2]   Reaction of Fischer carbene complexes with 1,3-butadiynes: A new strategem for biaryl synthesis with construction of the biaryl bond preceding synthesis of the arenes [J].
Bao, JM ;
Wulff, WD ;
Fumo, MJ ;
Grant, EB ;
Heller, DP ;
Whitcomb, MC ;
Yeung, SM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (09) :2166-2181
[3]   Asymmetric conjugate nucleophilic addition of organolithiums to chromium (menthyloxy)(aryl)carbene complexes [J].
Barluenga, J ;
Trabanco, AA ;
Florez, J ;
GarciaGranda, S ;
Martin, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) :13099-13100
[4]   Physical organic chemistry of transition metal carbene complexes .7. Kinetics of hydrolysis of (CO)(5)M=C(OR)Ph (M=Cr, W; R=Me, Et) and (CO)(5)Cr=(OMe)CH=CHPh in aqueous acetonitrile [J].
Bernasconi, CF ;
Flores, FX ;
Kittredge, KW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2103-2110
[5]   SUBSTRATE REGULATION OF PRODUCT DISTRIBUTION IN THE REACTIONS OF ARYL CHROMIUM CARBENE COMPLEXES WITH ALKYNES [J].
BOS, ME ;
WULFF, WD ;
MILLER, RA ;
CHAMBERLIN, S ;
BRANDVOLD, TA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9293-9319
[6]   SYNTHESIS OF "ALPHA-METHYLENE-GAMMA-BUTYROLACTONE VIA TRANSITION-METAL CARBENE COMPLEXES [J].
CASEY, CP ;
BRUNSVOLD, WR .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 102 (02) :175-183
[7]   SOLVENT, CHELATION AND CONCENTRATION EFFECTS ON THE BENZANNULATION REACTION OF CHROMIUM CARBENE COMPLEXES AND ACETYLENES [J].
CHAN, KS ;
PETERSON, GA ;
BRANDVOLD, TA ;
FARON, KL ;
CHALLENER, CA ;
HYLDAHL, C ;
WULFF, WD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 334 (1-2) :9-56
[8]  
CONNOR JA, 1971, J CHEM SOC CHEM COMM, P570
[9]   STABILISATION OF NUCLEOPHILIC CARBENES CO-ORDINATED TO TRANSITION METALS [J].
CONNOR, JA ;
JONES, EM .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1971, (12) :1974-+
[10]  
de Meijere A, 2000, ANGEW CHEM INT EDIT, V39, P3964, DOI 10.1002/1521-3773(20001117)39:22<3964::AID-ANIE3964>3.0.CO