Efficient synthesis of functionalized 4,5-benzotropones by regioselective cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with phthalic dialdehyde

被引:0
作者
Langer, P [1 ]
Albrecht, U [1 ]
机构
[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany
关键词
aldol reactions; benzotropones; cyclizations; regioselectivity; silyl enol ethers;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of 1,3-bis(trimethylsiloxy)-1,3-butadienes with phthalic dialdehyde resulted in regioselective formation of functionalized 4,5-benzotropones.
引用
收藏
页码:526 / 528
页数:3
相关论文
共 25 条
[1]  
ASAO T, 1993, METHOD ORGAN CHEM, V5, P728
[2]   TOTAL SYNTHESES OF THE STRUCTURES ASSIGNED TO SALIMINE AND JERUSALEMINE, ALKALOIDS FROM COLCHICUM-DECAISNEI BOISS (LILIACEAE) [J].
BANWELL, MG ;
FAM, MA ;
GABLE, RW ;
HAMEL, E .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (22) :2647-2649
[3]  
Boye O., 1992, The Alkaloids, V41, P125
[4]   CHEMISTRY OF ENOL SILYL ETHERS .5. A NOVEL CYCLOAROMATIZATION REACTION - REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED METHYL SALICYLATES [J].
CHAN, TH ;
BROWNBRIDGE, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (10) :3534-3538
[5]   CONDENSATION OF O-PHTHALALDEHYDE WITH KETONES .1. FORMATION AND STRUCTURES OF SOME 4,5-BENZTROPONES [J].
DAVEY, W ;
GOTTFRIED, H .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (10) :3699-&
[6]   MECHANISM OF PURPUROGALLIN FORMATION - AN ADDUCT FROM 3-HYDROXY-ORTHO-BENZOQUINONE AND 4,5-DIMETHYL-ORTHO-BENZOQUINONE [J].
DURCKHEIMER, W ;
PAULUS, EF .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (03) :224-225
[7]  
FOHLISCH B, 1972, SYNTH-INT J METHODS, P564
[8]  
Gill M, 1987, Fortschr Chem Org Naturst, V51, P1
[9]  
Klostermeyer D, 2000, EUR J ORG CHEM, V2000, P603
[10]   Chemo- and regio-selective synthesis of functionalized 3(2H)-furanones by the first cyclization reactions of 1,3-bis(trimethylsiloxy)buta-1,3-dienes with α-chlorocarboxylic acid chlorides [J].
Langer, P ;
Krummel, T .
CHEMICAL COMMUNICATIONS, 2000, (11) :967-968