Synthesis of ethyl 3-cyano-2-methylcinnamates and 3-cyano-2-methylcinnamonitriles from the Baylis-Hillman acetates

被引:79
作者
Chung, YM
Gong, JH
Kim, TH
Kim, JN [1 ]
机构
[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea
[2] Chonnam Natl Univ, Inst Basic Sci, Kwangju 500757, South Korea
[3] Chonnam Natl Univ, Fac Appl Chem, Kwangju 500757, South Korea
基金
新加坡国家研究基金会;
关键词
Baylis-Hillman acetates; ethyl; 3-cyano-2-methylcinnamates; DABCO;
D O I
10.1016/S0040-4039(01)01971-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of the DABCO salts 2, generated in situ from the Baylis-Hillman acetates 1, and KCN in aqueous THF gave ethyl 3-cyano-2-methylcinnamates 4a-d and 3-cyano-2-methylcinnamonitriles 4e-f in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9023 / 9026
页数:4
相关论文
共 23 条
[1]   AMINO-GROUPS IMMOBILIZED ON SILICA-GEL - AN EFFICIENT AND REUSABLE HETEROGENEOUS CATALYST FOR THE KNOEVENAGEL CONDENSATION [J].
ANGELETTI, E ;
CANEPA, C ;
MARTINETTI, G ;
VENTURELLO, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01) :105-107
[2]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[3]   The Baylis-Hillman chemistry in aqueous media: a convenient synthesis of 2-methylenealkanoates and alkanenitriles [J].
Basavaiah, D ;
Kumaragurubaran, N .
TETRAHEDRON LETTERS, 2001, 42 (03) :477-479
[4]   Baylis-Hillman chemistry: a novel synthesis of functionalized 1,4-pentadienes [J].
Basavaiah, D ;
Kumaragurubaran, N ;
Sharada, DS .
TETRAHEDRON LETTERS, 2001, 42 (01) :85-87
[5]   KNOEVENAGEL CONDENSATION IN THE HETEROGENEOUS PHASE USING ALPO4-AL2O3 AS A NEW CATALYST [J].
CABELLO, JA ;
CAMPELO, JM ;
GARCIA, A ;
LUNA, D ;
MARINAS, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5195-5197
[6]   A one pot synthesis of (E)-4-alkylidene-2-cyclohexen-1-ones [J].
Chamakh, A ;
Amri, H .
TETRAHEDRON LETTERS, 1998, 39 (5-6) :375-378
[7]  
Ciganek E., 1997, ORG REACTIONS, V51, P201
[8]   Silica gel catalysed Knoevenagel condensation in Dry Media under microwave irradiation [J].
delaCruz, P ;
DiezBarra, E ;
Loupy, A ;
Langa, F .
TETRAHEDRON LETTERS, 1996, 37 (07) :1113-1116
[9]   SYNTHETIC POTENTIAL OF THE TERTIARY-AMINE-CATALYSED REACTION OF ACTIVATED VINYL CARBANIONS WITH ALDEHYDES [J].
DREWES, SE ;
ROOS, GHP .
TETRAHEDRON, 1988, 44 (15) :4653-4670
[10]   Reaction of 2-formyl imidazole with intermediates from the Baylis-Hillman reaction [J].
Drewes, SE ;
Horn, MM ;
Ramesar, N .
SYNTHETIC COMMUNICATIONS, 2000, 30 (06) :1045-1055