Epoxidation of chromones and flavonoids in ionic liquids

被引:24
作者
Bernini, R
Mincione, E
Coratti, A
Fabrizi, G
Battistuzzi, G
机构
[1] Univ Tuscia, Dipartimento Agrobiol & Agrochim, I-01100 Viterbo, Italy
[2] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Sostanze Biologicament, I-00185 Rome, Italy
关键词
epoxidation; chromones; flavonoids; chalcones; isoflavones; ionic liquids; bmim]BF4;
D O I
10.1016/j.tet.2003.11.032
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and efficient procedure for the epoxidation of chromone, isoflavone, and chalcone derivatives using 1-butyl-3-methyl imidazolium tetrafluoroborate [bmim]BF4 as solvent and alkaline hydrogen peroxide as oxidant is described. All reactions proceed in good yields and faster than in conventional solvents. No evidence of formation of compounds derived from the opening of the epoxide ring was attained. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:967 / 971
页数:5
相关论文
共 73 条
[1]   Asymmetric Weitz-Scheffer epoxidation of isoflavones with hydroperoxides mediated by optically active phase-transfer catalysts [J].
Adam, W ;
Rao, PB ;
Degen, HG ;
Levai, A ;
Patonay, T ;
Saha-Möller, CR .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :259-264
[2]  
ADAM W, 1992, SYNTHESIS-STUTTGART, P436
[3]   Enantioselective epoxidation of isoflavones by Jacobsen's Mn(III)salen catalysts and dimethyldioxirane oxygen-atom source [J].
Adam, W ;
Fell, RT ;
Lévai, A ;
Patonay, T ;
Peters, K ;
Simon, A ;
Tóth, G .
TETRAHEDRON-ASYMMETRY, 1998, 9 (07) :1121-1124
[4]  
ADAM W, 1995, LIEBIGS ANN, P1547
[5]   DIMETHYLDIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES, ACIDS AND ESTERS [J].
ADAM, W ;
HADJIARAPOGLOU, L ;
NESTLER, B .
TETRAHEDRON LETTERS, 1990, 31 (03) :331-334
[6]   Asymmetric Weitz-Scheffer epoxidation of conformationally flexible and fixed enones with sterically demanding hydroperoxides mediated by optically active phase-transfer catalysts [J].
Adam, W ;
Rao, PB ;
Degen, HG ;
Saha-Möller, CR .
TETRAHEDRON-ASYMMETRY, 2001, 12 (01) :121-125
[7]   DIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES [J].
ADAM, W ;
HADJIARAPOGLOU, L ;
SMERZ, A .
CHEMISCHE BERICHTE, 1991, 124 (01) :227-232
[8]   DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].
ADAM, W ;
CURCI, R ;
EDWARDS, JO .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211
[9]   Catalytic asymmetric epoxidation of enones under phase-transfer catalyzed conditions [J].
Arai, S ;
Tsuge, H ;
Oku, M ;
Miura, M ;
Shioiri, T .
TETRAHEDRON, 2002, 58 (08) :1623-1630
[10]   EPOXIDATION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY DIMETHYLDIOXIRANE [J].
BAUMSTARK, AL ;
HARDEN, DB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7615-7618