Recent Advances in Green Synthesis of 3,3′-Spirooxindoles via Isatin-based One-pot Multicomponent Cascade Reactions in Aqueous Medium

被引:86
作者
Yan, Li-Jun [1 ]
Wang, Yong-Chao [1 ]
机构
[1] Yunnan Normal Univ, Sch Vocat & Tech Educ, Kunming 650092, Peoples R China
关键词
3,3 '-spirooxindole; Aqueous medium; Catalyst; Green synthesis; Multicomponent cascade reaction; UREA-SALT MIXTURES; CROSS-COUPLING REACTIONS; STRUCTURE-BASED DESIGN; DIELS-ALDER REACTIONS; CATALYZED ONE-POT; 3-COMPONENT SYNTHESIS; SPIROOXINDOLE DERIVATIVES; ORGANIC-REACTIONS; HETEROGENEOUS CATALYST; REUSABLE NANOCATALYST;
D O I
10.1002/slct.201601534
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
3,3'-spirooxindoles are important synthetic target compounds and play special role in organic chemistry because of their extensive biological activities and applications of pharmaceutical lead discovery. In recent years, there has been a significant increase in design of new, atom economical and eco-friendly isatin-based one-pot multicomponent cascade reactions in aqueous medium for the green synthesis of 3,3'-spirooxindoles. In this review, the recent advances in this area were summarized and classified according to catalyst-free, organiccatalyzed, inorganic-catalyzed, nanometer-silica-catalyzed and enzyme-catalyzed reaction systems. These reviewed methods provide important inspiration for the synthesis of novel 3,3'spirooxindoles and design of new pharmaceutical compounds.
引用
收藏
页码:6948 / 6960
页数:13
相关论文
共 128 条
[1]   Glycerol eutectics as sustainable solvent systems [J].
Abbott, Andrew P. ;
Harris, Robert C. ;
Ryder, Karl S. ;
D'Agostino, Carmine ;
Gladden, Lynn F. ;
Mantle, Mick D. .
GREEN CHEMISTRY, 2011, 13 (01) :82-90
[2]   Synthesis and antimicrobial activity of some new pyrazole, fused pyrazolo[3,4-d]-pyrimidine and pyrazolo[4,3-e][1,2,4]triazolo[1,5-c] pyrimidine derivatives [J].
Abunada, Nada M. ;
Hassaneen, Hamdi M. ;
Kandile, Nadia G. ;
Miqdad, Omar A. .
MOLECULES, 2008, 13 (07) :1501-1517
[3]   Synthesis of spiro[benzopyrazolonaphthyridine-indoline]-diones and spiro[chromenopyrazolopyridine-indoline]-diones by one-pot, three-component methods in water [J].
Ahadi, Somayeh ;
Ghahremanzadeh, Ramin ;
Mirzaei, Peiman ;
Bazgir, Ayoob .
TETRAHEDRON, 2009, 65 (45) :9316-9321
[4]   New four-component reactions in water: a convergent approach to the metal-free synthesis of spiro[indoline/acenaphthylene-3,4′-pyrazolo[3,4-b]pyridine derivatives [J].
Balarnurugan, Kamaraj ;
Perumal, Subbu ;
Menendez, J. Carlos .
TETRAHEDRON, 2011, 67 (18) :3201-3208
[5]   Copper Ferrite Nanoparticles: An Efficient and Reusable Nanocatalyst for a Green One-Pot, Three-component Synthesis of Spirooxindoles in Water [J].
Bazgir, Ayoob ;
Hosseini, Ghaffar ;
Ghahremanzadeh, Ramin .
ACS COMBINATORIAL SCIENCE, 2013, 15 (10) :530-534
[6]   Ultrasound-assisted one-pot, three-component synthesis of spiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-2,6′(1′H)-diones in water [J].
Bazgir, Ayoob ;
Ahadi, Somayeh ;
Ghahremanzadeh, Ramin ;
Khavasi, Hamid Reza ;
Mirzaei, Peiman .
ULTRASONICS SONOCHEMISTRY, 2010, 17 (02) :447-452
[7]   LIGAND-ACCELERATED CATALYSIS [J].
BERRISFORD, DJ ;
BOLM, C ;
SHARPLESS, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (10) :1059-1070
[8]  
Boer Rainer, 1995, Drugs of the Future, V20, P499
[9]   Protonated chiral catalysts: Versatile tools for asymmetric synthesis [J].
Bolm, C ;
Rantanen, T ;
Schiffers, I ;
Zani, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (12) :1758-1763
[10]   Carbon-carbon bonds by hydrolytic enzymes [J].
Branneby, C ;
Carlqvist, P ;
Magnusson, A ;
Hult, K ;
Brinck, T ;
Berglund, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (04) :874-875