Three-component one-pot synthesis of pyrazolo[3,4-b]quinolin-5(6H)-one derivatives in aqueous media

被引：24
作者：
Wang, Hui-Yan [1 ]
Shi, Da-Qing [1 ]
机构：
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2012年 / 49卷 / 01期
关键词：
DIELS-ALDER REACTIONS; CLEAN SYNTHESIS; MULTICOMPONENT REACTIONS; SPIROOXINDOLE DERIVATIVES; CONDENSATION REACTION; ORGANIC-REACTIONS; MELDRUMS ACID; EFFICIENT; WATER; ALDEHYDES;
D O I：
10.1002/jhet.781
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of 4-aryl-3,7,7-trimethyl-1-phenyl-7,8-dihydro-1H-pyrazolo[3,4-b]quinolin- 5(6H)-ones were synthesized by the three-component reaction of aromatic aldehydes, 3-methyl-1-phenyl-1H-pyrazol-5-amine, and 5,5-dimethyl-1,3-cyclohexandione in the presence of sodium 1-dodecanesulfonate in aqueous medium. Compared to the previous methods, this new protocol has the advantages of convenient operation, higher yields, lower cost, and environmentally benign procedure. J. Heterocyclic Chem., (2012).
引用
收藏
页码：212 / 216
页数：5
相关论文
共 53 条
[1]  
Amato J., 1993, SCIENCE, V259, P1538
[2]   A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines [J].
Bagley, MC ;
Dale, JW ;
Bower, J .
CHEMICAL COMMUNICATIONS, 2002, (16) :1682-1683
[3]   The Michael reaction of nitroalkanes with conjugated enones in aqueous media [J].
Ballini, R ;
Bosica, G .
TETRAHEDRON LETTERS, 1996, 37 (44) :8027-8030
[4]   A novel metal iodide promoted three-component synthesis of substituted pyrrolidines [J].
Bertozzi, F ;
Gustafsson, M ;
Olsson, R .
ORGANIC LETTERS, 2002, 4 (18) :3147-3150
[5]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[6]  
2-A
[7]   Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the knoevenagel synthesis of coumarin-3-carboxylic acids [J].
Bigi, F ;
Chesini, L ;
Maggi, R ;
Sartori, G .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1033-1035
[8]   Clean synthesis in water. Part 2: Uncatalysed condensation reaction of Meldrum's acid and aldehydes [J].
Bigi, F ;
Carloni, S ;
Ferrari, L ;
Maggi, R ;
Mazzacani, A ;
Sartori, G .
TETRAHEDRON LETTERS, 2001, 42 (31) :5203-5205
[9]   A novel microwave-mediated one-pot synthesis of indolizines via a three-component reaction [J].
Bora, U ;
Saikia, A ;
Boruah, RC .
ORGANIC LETTERS, 2003, 5 (04) :435-438
[10]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
123456