A straightforward method for the synthesis of alkylidene and arylidene malonates through proline-catalyzed knoevenagel condensation

被引:99
作者
Cardillo, G [1 ]
Fabbroni, S [1 ]
Gentilucci, L [1 ]
Gianotti, M [1 ]
Tolomelli, A [1 ]
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
关键词
knoevenagel condensation; proline; alkylidene malonate; arylidene malonate; arylidene cyanoacetate;
D O I
10.1081/SCC-120018782
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A straightforward method for the synthesis of alkylidene/arylidene malonates and arylidene cyanoacetates, utilizing proline as an alternative to traditional catalysts is presented. A large number of unsaturated esters was obtained from the Knoevenagel reaction under very mild conditions and utilizing cheap reagents.
引用
收藏
页码:1587 / 1594
页数:8
相关论文
共 26 条
[1]   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
[2]   Conjugate addition of hydroxylamino derivatives to alkylidene malonates in the presence of chiral Lewis acids [J].
Cardillo, G ;
Gentilucci, L ;
Gianotti, M ;
Kim, H ;
Perciaccante, R ;
Tolomelli, A .
TETRAHEDRON-ASYMMETRY, 2001, 12 (17) :2395-2398
[3]   Synthesis of aziridine-2,2-dicarboxylates via 1,4-addition of N,O-(bistrimethylsilyl)hydroxylamine to α,β-unsaturated malonates [J].
Cardillo, G ;
Gentilucci, L ;
Gianotti, M ;
Perciaccante, R ;
Tolomelli, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8657-8660
[4]   Catalytic C-C bond formation promoted by Mg-Al-O-t-Bu hydrotalcite [J].
Choudary, BM ;
Kantam, ML ;
Kavita, B ;
Reddy, CV ;
Figueras, F .
TETRAHEDRON, 2000, 56 (47) :9357-9364
[5]   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
[6]   HARD ACID AND SOFT NUCLEOPHILE SYSTEMS .9. CLEAVAGE OF ACTIVATED CARBON-CARBON DOUBLE-BONDS WITH A HARD LEWIS ACID AND ETHANETHIOL [J].
FUJI, K ;
KAWABATA, T ;
NODE, M ;
FUJITA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) :3214-3216
[7]  
Gröger H, 2001, ANGEW CHEM INT EDIT, V40, P529
[8]   Optically active esters of beta-ketonic and beta aldehydic acids Part IV Condensation of aldehydes with menthyl acetoacetate [J].
Hann, ACO ;
Lapworth, A .
JOURNAL OF THE CHEMICAL SOCIETY, 1904, 85 :46-56
[9]   Steric effects in high pressure Knoevenagel reactions [J].
Jenner, G .
TETRAHEDRON LETTERS, 2001, 42 (02) :243-245
[10]  
KNOEVENAGEL E, 1898, CHEM BER, V31, P2585