Rapid parallel synthesis of polymer-bound enones utilizing microwave-assisted solid-phase chemistry

被引:72
作者
Strohmeier, GA [1 ]
Kappe, CO [1 ]
机构
[1] Graz Univ, Inst Chem, A-8010 Graz, Austria
来源
JOURNAL OF COMBINATORIAL CHEMISTRY | 2002年 / 4卷 / 02期
关键词
D O I
10.1021/cc010043r
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A microwave-assisted parallel solid-phase synthesis of a collection of 21 polymer-bound enones has been developed. The two-step protocol involves initial high-speed acetoacetylation of polystyrene Wang resin with a selection of seven common beta-ketoesters. When microwave flash heating at 170 C was employed, complete conversions were achieved within 1-10 min, a significant improvement over the conventional thermal method. which takes several hours for completion. Significant rate enhancements were also observed for the subsequent microwave-heated Knoevenagel condensations with a second set of 13 different aldehydes. Reaction times were reduced to 30-60 min at 125 degreesC in the microwave protocol compared to 1-2 days using conventional thermal conditions. Kinetic comparison studies indicate that the observed rate enhancements can be attributed to the rapid direct heating of the solvent (1,2-dichlorobenzene) by microwaves rather than to any specific microwave effect. All reactions have been carried out in commercially available parallel reactors with on-line temperature measurement, designed specifically for use in multimode microwave cavities.
引用
收藏
页码:154 / 161
页数:8
相关论文
共 64 条
[21]   Photoacoustic FTIR spectroscopy, a nondestructive method for sensitive analysis of solid-phase organic chemistry [J].
Gosselin, F ;
DiRenzo, M ;
Ellis, TH ;
Lubell, WD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :7980-7981
[22]  
Grosche P, 1999, SYNTHESIS-STUTTGART, P1961
[23]   High-throughput 1H NMR and HPLC characterization of a 96-member substituted methylene malonamic acid library [J].
Hamper, BC ;
Snyderman, DM ;
Owen, TJ ;
Scates, AM ;
Owsley, DC ;
Kesselring, AS ;
Chott, RC .
JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (02) :140-150
[24]   Solid phase synthesis of dihydropyrimidinones and pyrimidinone carboxylic acids from malonic acid resin [J].
Hamper, BC ;
Gan, KZ ;
Owen, TJ .
TETRAHEDRON LETTERS, 1999, 40 (27) :4973-4976
[25]   Solid phase synthesis of 2-aminobutadienes using a piperazine linker [J].
Hird, NW ;
Irie, K ;
Nagai, K .
TETRAHEDRON LETTERS, 1997, 38 (40) :7111-7114
[26]   Microwave-assisted solid-phase Ugi four-component condensations [J].
Hoel, AML ;
Nielsen, J .
TETRAHEDRON LETTERS, 1999, 40 (20) :3941-3944
[27]  
Jones G., 1967, ORGANICREACTIONS, V15, P204, DOI [DOI 10.1002/0471264180.OR015.02, 10.1002/0471264180.or015.02]
[28]  
Kappe CO, 2001, AM LAB, V33, P13
[29]  
KAPPE CO, IN PRESS CURR OPIN C
[30]   The preparation of resin-bound nitroalkenes and some applications in high pressure promoted cycloadditions [J].
Kuster, GJ ;
Scheeren, HW .
TETRAHEDRON LETTERS, 2000, 41 (04) :515-519