The implication of electrocatalysis in MCR strategy:: Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, aldehydes and malononitrile into substituted 5,6,7,8-tetrahydro-4H-chromenes

被引:52
作者
Elinson, Michail N. [1 ]
Dorofeev, Alexander S. [1 ]
Feducovich, Sergey K. [1 ]
Gorbunov, Sergey V. [1 ]
Nasybullin, Ruslan F. [1 ]
Miloserdov, Fedor M. [1 ]
Nikishin, Gennady I. [1 ]
机构
[1] ND Zelinskii Inst Organ Chem, Leninsky Prospekt 47, Moscow 119991, Russia
关键词
oxygen heterocycles; electrochemistry; homogeneous catalysis; multicomponent reactions; cyclization;
D O I
10.1002/ejoc.200600544
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
The electrochemically induced catalytic multicomponent transformation of cyclic 1,3-diketones, aldehydes and malononitrile in alcoholic solvents results in the formation of substituted 5,6,7,8-tetrahydro-4H-chromenes in 85-95% yields. The reaction is performed in an undivided cell in the presence of sodium bromide as an electrolyte. The application of this efficient electrocatalytic method to the formation of tetrahydro-4H-chromenes is beneficial for diversity-oriented large-scale processes. The novel concept of an electrocatalytic multicomponent reaction is also ecologically sound. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).
引用
收藏
页码:4335 / 4339
页数:5
相关论文
共 33 条
[1]
Abdel-Latif F. F., 1995, J CHEM RES MINIPRINT, P1220
[2]
ADREANI LL, 1960, B CHIM FARM, V99, P583
[3]
(S)-Proline as a neutral and efficient catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media [J].
Balalaie, S ;
Bararjanian, M ;
Amani, AM ;
Movassagh, B .
SYNLETT, 2006, (02) :263-266
[4]
Pd-assisted multicomponent synthesis of heterocycles [J].
Balme, G ;
Bossharth, E ;
Monteiro, N .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4101-4111
[5]
SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 2-OXO-(2H) 1-BENZOPYRAN-3-CARBOXAMIDE DERIVATIVES [J].
BONSIGNORE, L ;
LOY, G ;
SECCI, D ;
CALIGNANO, A .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (06) :517-520
[6]
The recent impact of solid-phase synthesis on medicinally relevant benzoannelated nitrogen heterocycles [J].
Bräse, S ;
Gil, C ;
Knepper, K .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) :2415-2437
[7]
Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions [J].
Devi, I ;
Bhuyan, PJ .
TETRAHEDRON LETTERS, 2004, 45 (47) :8625-8627
[8]
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[9]
2-U
[10]
Stereoselective electrocatalytic cyclization of 3-substituted 2,2-dicyanocyclopropane-1,1-dicarboxylic acid esters to form 6-substituted (1R,5R,6R)*-4,4-dialkoxy-5-cyano-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid esters [J].
Elinson, M. N. ;
Fedukovich, S. K. ;
Starikova, Z. A. ;
Vereshchagin, A. N. ;
Belyakov, P. A. ;
Gorbunov, S. V. ;
Nikishin, G. I. .
RUSSIAN CHEMICAL BULLETIN, 2006, 55 (01) :106-111