CuSO4-catalyzed three-component reaction of α-diazo ester, water and isatin: an efficient approach to oxindole derivatives

被引:32
作者
Jing, Changcheng [1 ]
Shi, Taoda [1 ]
Xing, Dong [1 ]
Guo, Xin [1 ]
Hu, Wen-Hao [1 ]
机构
[1] E China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Shanghai 200062, Peoples R China
基金
美国国家科学基金会;
关键词
C-H INSERTION; PROTEASOME INHIBITORS; TRANSFER HYDROGENATION; ORGANIC-REACTIONS; AQUEOUS-MEDIA; ALKALOIDS; TMC-95A; DIKETOPIPERAZINES; WELWITINDOLINONES; REARRANGEMENT;
D O I
10.1039/c2gc36708d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly efficient three-component reaction of alpha-diazo ester, water and isatin was developed by using CuSO4 as the catalyst. In this reaction, water was used as both a reactant and the solvent. With this highly environmentally benign and economical protocol, a series of 3-hydroxyindolin-2-one derivatives were efficiently produced in good yields with moderate to high diastereoselectivities.
引用
收藏
页码:620 / 624
页数:5
相关论文
共 72 条
[21]   Facile synthesis of aryl α-keto esters via the reaction of aryl diazoacetate with H2O and DEAD [J].
Guo, Zhenqiu ;
Huang, Haoxi ;
Fu, Qingquan ;
Hu, Wenhao .
SYNLETT, 2006, (15) :2486-2488
[22]   Component match in rhodium catalyzed three-component reactions of ethyl diazoacetate, H2O and aryl imines: a highly diastereoselective one-step synthesis of β-aryl isoserine derivatives [J].
Guo, Zhenqiu ;
Shi, Taoda ;
Jiang, Jun ;
Yang, Liping ;
Hu, Wenhao .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (23) :5028-5033
[23]   Reactions of C-H bonds in water [J].
Herrerias, Clara I. ;
Yao, Xiaoquan ;
Li, Zhiping ;
Li, Chao-Jun .
CHEMICAL REVIEWS, 2007, 107 (06) :2546-2562
[24]   A Water-Soluble Ruthenium Glycosylated Porphyrin Catalyst for Carbenoid Transfer Reactions in Aqueous Media with Applications in Bioconjugation Reactions [J].
Ho, Chi-Ming ;
Zhang, Jun-Long ;
Zhou, Cong-Ying ;
Chan, On-Yee ;
Yan, Jessie Jing ;
Zhang, Fu-Yi ;
Huang, Jie-Sheng ;
Che, Chi-Ming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) :1886-1894
[25]   Searching for green solvents [J].
Jessop, Philip G. .
GREEN CHEMISTRY, 2011, 13 (06) :1391-1398
[26]   Organocatalytic asymmetric three-component cyclization of cinnamaldehydes and primary amines with 1,3-dicarbonyl compounds: Straightforward access to enantiomerically enriched dihydropyridines [J].
Jiang, Jun ;
Yu, Jie ;
Sun, Xi-Xi ;
Rao, Qin-Quan ;
Gong, Liu-Zhu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (13) :2458-2462
[27]   Oxidized welwitindolinones from terrestrial Fischerella spp. [J].
Jimenez, JI ;
Huber, U ;
Moore, RE ;
Patterson, GML .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (04) :569-572
[28]   Palladium acetate immobilized in a hierarchical MFI zeolite-supported ionic liquid: a highly active and recyclable catalyst for Suzuki reaction in water [J].
Jin, Myung-Jong ;
Taher, Abu ;
Kang, Hee-Jae ;
Choi, Minkee ;
Ryoo, Ryong .
GREEN CHEMISTRY, 2009, 11 (03) :309-313
[29]   Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization-Claisen rearrangement of 2-allyloxyindolin-3-ones [J].
Kawasaki, T ;
Nagaoka, M ;
Satoh, T ;
Okamoto, A ;
Ukon, R ;
Ogawa, A .
TETRAHEDRON, 2004, 60 (15) :3493-3503
[30]   TMC-95A, B, C, and D, novel proteasome inhibitors produced by Apiospora montagnei Sacc. TC 1093 -: Taxonomy, production, isolation, and biological activities [J].
Koguchi, Y ;
Kohno, J ;
Nishio, M ;
Takahashi, K ;
Okuda, T ;
Ohnuki, T ;
Komatsubara, S .
JOURNAL OF ANTIBIOTICS, 2000, 53 (02) :105-109