An efficient synthesis of 2-diazo-2-(trimethylsilyl)ethanols and their application to pyrazole synthesis

被引：45
作者：
Hari, Yoshiyuki [1 ]
Tsuchida, Susumu [1 ]
Sone, Ryosuke [1 ]
Aoyama, Toyohiko [1 ]
机构：
[1] Nagoya City Univ, Grad Sch Pharmaceut Sci, Nagoya, Aichi 4678603, Japan
来源：
SYNTHESIS-STUTTGART | 2007年 / 21期
关键词：
diazoalcohol; 2-diazo-2-(trimethylsilyl)ethanols; diazo(trimethylsilyl)methylmagnesium bromide; pyrazoles; trimethylsilyldiazomethane;
D O I：
10.1055/s-2007-990817
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of diazo(trimethylsilyl)methylmagnesium bromide with aldehydes or ketones gave 2-diazo-2-(trimethylsilyl)ethanols, which were applied to the synthesis of di- and trisubstituted pyrazoles via [3+2] cycloaddition reaction with ethyl propiolate or dimethyl acetylenedicarboxylate.
引用
收藏
页码：3371 / 3375
页数：5
相关论文
共 22 条
[1]   TRANSITION-METAL-CATALYZED DECOMPOSITION OF DIAZO(TRIALKYLSILYL)-ACETATES - INTERMOLECULAR FORMATION AND TRAPPING OF CARBONYL YLIDES [J].
ALT, M ;
MAAS, G .
TETRAHEDRON, 1994, 50 (25) :7435-7444
[2]   TRIMETHYLSILYLDIAZOMETHANE - A CONVENIENT REAGENT FOR THE PREPARATION OF (E)-1-TRIMETHYLSILYL-1-ALKENES [J].
AOYAMA, T ;
SHIOIRI, T .
TETRAHEDRON LETTERS, 1988, 29 (48) :6295-6296
[3]   NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .62. TRIMETHYLSILYLDIAZOMETHANE - A CONVENIENT REAGENT FOR THE PREPARATION OF ACYLSILANES [J].
AOYAMA, T ;
SHIOIRI, T .
TETRAHEDRON LETTERS, 1986, 27 (18) :2005-2006
[4]  
AOYAMA T, 1981, CHEM PHARM BULL, V29, P3249
[5]   NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .8. TRIMETHYLSILYLDIAZOMETHANE, A NEW, STABLE, AND SAFE REAGENT FOR THE CLASSICAL ARNDT-EISTERT SYNTHESIS [J].
AOYAMA, T ;
SHIOIRI, T .
TETRAHEDRON LETTERS, 1980, 21 (46) :4461-4462
[6]  
AOYAMA T, 1989, J CHEM SOC P1, V37, P2261
[7]   Intermolecular rhodium(II)-catalyzed reactions with silicon-substituted carbonyl ylides [J].
Bolm, C ;
Saladin, S ;
Kasyan, A .
ORGANIC LETTERS, 2002, 4 (26) :4631-4633
[8]   Synthesis and use of α-silyl-substituted α-hydroxyacetic acids [J].
Bolm, C ;
Kasyan, A ;
Heider, P ;
Saladin, S ;
Drauz, K ;
Günther, K ;
Wagner, C .
ORGANIC LETTERS, 2002, 4 (13) :2265-2267
[9]  
Bolm C, 2000, ANGEW CHEM INT EDIT, V39, P2288, DOI 10.1002/1521-3773(20000703)39:13<2288::AID-ANIE2288>3.0.CO
[10]  
2-Y
123