Reaction of 2-methylene-1,3-dicarbonyl compounds containing a CF3-group with 1,3-dienes

被引:29
作者
Nenajdenko, VG [1 ]
Statsuk, AV [1 ]
Balenkova, ES [1 ]
机构
[1] Moscow State Univ, Dept Chem, Moscow 119899, Russia
关键词
Diels-Alder reaction; hetero-dienes; alpha; beta-unsannated ketones; trifluoromethyl ketones; 2-methylene-1,3-dicarbonyl compounds;
D O I
10.1016/S0040-4020(00)00605-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Knoevenagel condensation of 1-substituted 4,4,4-trifluorobutan-1,3-diones with paraformaldehyde in the presence of cyclic and Linear 1,3-dienes leads to Diels-Alder cycloadducts via in situ formation of the appropriate 2-methylene-1,3-dicarbonyl compounds 2(a-c). In the reactions with linear 1,3-dienes, compounds 2(a-c) react as dienophiles. In the case of the reactions with cyclic 1,3-dienes both normal and inverse demand Diels-Alder reactions take place. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6549 / 6556
页数:8
相关论文
共 33 条
[1]  
ARDIS AE, 1950, J AM CHEM SOC, P1305
[2]   Diethyl methylenemalonate [J].
Bachman, GB ;
Tanner, HA .
JOURNAL OF ORGANIC CHEMISTRY, 1939, 4 (04) :493-501
[3]   SYNTHESIS OF DI-TERT-BUTYL METHYLENEMALONATE, A STERICALLY HINDERED 1,1-DICARBONYL ALKENE [J].
BALLESTEROS, P ;
ROBERTS, BW ;
WONG, J .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20) :3603-3605
[4]   PREPARATION OF TRIFLUOROMETHYL KETONES AND RELATED FLUORINATED KETONES [J].
BEGUE, JP ;
BONNETDELPON, D .
TETRAHEDRON, 1991, 47 (20-21) :3207-3258
[5]   2 CONVENIENT METHODS FOR THE GENERATION OF METHYLENE MELDRUMS ACID FOR DIELS-ALDER REACTIONS [J].
BUZINKAI, JF ;
HRUBOWCHAK, DM ;
SMITH, FX .
TETRAHEDRON LETTERS, 1985, 26 (27) :3195-3198
[6]   Asymmetric Diels-Alder reaction of (S)-alpha-p-tolylsulfinyl alpha,beta-unsaturated esters: The role of the sulfinyl group in asymmetric Diels-Alder reactions of vinylsulfoxides [J].
Carretero, JC ;
Ruano, JLG ;
Cabrejas, LMM .
TETRAHEDRON-ASYMMETRY, 1997, 8 (13) :2215-2225
[7]  
COREY EJ, 1992, J AM CHEM SOC, V104, P6189
[8]   A VERSATILE AND CONVENIENT MULTIGRAM SYNTHESIS OF METHYLIDENEMALONIC ACID DIESTERS [J].
DEKEYSER, JL ;
DECOCK, CJC ;
POUPAERT, JH ;
DUMONT, P .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4859-4862
[9]  
DELUCCHI O, 1984, GAZZ CHIM ITAL, V114, P293
[10]   UNUSUAL TRANSFORMATIONS OF ETHYL-2-CYANOACRYLATE IN REACTIONS WITH TRIVALENT PHOSPHORUS-COMPOUNDS [J].
GOLOLOBOV, YG ;
KOLOMNIKOVA, GD ;
KRYLOVA, TO .
TETRAHEDRON LETTERS, 1994, 35 (11) :1751-1754