Silylated β-enaminones as precursors in the regioselective synthesis of silyl pyrazoles

被引:42
作者
Calle, M [1 ]
Calvo, LA [1 ]
González-Ortega, A [1 ]
González-Nogal, AM [1 ]
机构
[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, Valladolid 47011, Spain
关键词
silicon isoxazoles; silicon beta-enaminones; silicon pyrazoles;
D O I
10.1016/j.tet.2005.10.001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Silyl beta-enaminones have been synthesized by reductive cleavage of 5-silyl, 3-, 4- and 5-silyliiiethylisoxazoles. These versatile synthons bearing different silyl groups in various positions of the enaminoketonic system are of great interest in the regioselective synthesis of 3- or 5-silylpyrazoles and 3-, 4- or 5-silylmethylpyrazoles, which can serve as building blocks in heterocyclic chemistry. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:611 / 618
页数:8
相关论文
共 8 条
[1]   Reaction of dianions of acyclic beta-enamino ketones with electrophiles .8(a). Synthesis of trialkylsilylenaminones and alpha'-silylated beta-diketones [J].
Bartoli, G ;
Bosco, M ;
Dalpozzo, R ;
DeNino, A ;
Iantorno, E ;
Tagarelli, A ;
Palmieri, G .
TETRAHEDRON, 1996, 52 (27) :9179-9186
[2]  
BIRKOFER L, 1980, TOP CURR CHEM, V88, P62
[3]  
Calle M, 2001, SYNTHESIS-STUTTGART, P1949
[4]   Synthesis of silylated β-enaminones and applications to the synthesis of silyl heterocycles [J].
Calvo, LA ;
González-Nogal, AM ;
González-Ortega, A ;
Sañudo, MC .
TETRAHEDRON LETTERS, 2001, 42 (51) :8981-8984
[5]   Regiospecific synthesis of 5-silyl azoles [J].
Cuadrado, P ;
González-Nogal, AM ;
Valero, R .
TETRAHEDRON, 2002, 58 (24) :4975-4980
[6]  
HOPPE I, 1979, LIEBIGS ANN CHEM, P219
[7]   STEREOSPECIFIC SYNTHESIS OF (E)-ALKENYLPYRIDINES VIA ALPHA-SILYL CARBANION [J].
KONAKAHARA, T ;
TAKAGI, Y .
TETRAHEDRON LETTERS, 1980, 21 (21) :2073-2076
[8]   GROUP-IVB ORGANOMETALLIC DERIVATIVES - SYNTHESIS AND C-13 NMR-SPECTRA OF NEW SILYL AND STANNYL ISOXAZOLES [J].
NESI, R ;
RICCI, A ;
TADDEI, M ;
TEDESCHI, P .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 195 (03) :275-283