Green Protocols for the Synthesis of 3,3′-spirooxindoles - 2016- mid 2019

被引:20
作者
Deepthi, Ani [1 ]
Thomas, Noble, V [1 ]
Sathi, Vidya [1 ]
机构
[1] Univ Kerala, Dept Chem, Thiruvananthapuram 695581, Kerala, India
关键词
3,3 '-spirooxindoles; multicomponent reactions; spiropyrans; spiropyrrolidines; catalysts; green; ONE-POT SYNTHESIS; HIGHLY FUNCTIONALIZED SPIROOXINDOLE; POLYETHYLENE-GLYCOL PEG-400; CERIUM(IV) AMMONIUM-NITRATE; MULTICOMPONENT REACTION; BIS-SPIROOXINDOLES; CATALYST-FREE; C-H; 4-COMPONENT SYNTHESIS; EFFICIENT CATALYST;
D O I
10.2174/2213346106666191019144116
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Spirooxindoles, particularly 3,3'-spirooxindoles constitute a privileged structural scaffold owing to the intensive biological activities which they possess. Because of this over the last twenty years, a large number of methods were devised for their synthesis and some of these molecules have entered pre-clinical trials. Of late, methods for spirooxindole synthesis using green protocols have developed rapidly. Reactions based on multicomponent strategies using non-catalytic / biocatalytic pathways and those done in aqueous media have been largely employed for the synthesis of 3,3'-spirooxindoles. This review focusses on the synthesis of 3,3'-spirooxindoles via green protocols and covers the literature from 2016 onwards (2016 - mid 2019); a review on the same topic has appeared in 2016. The green methods discussed here include reactions done in aqueous media, multicomponent strategies, alternate solvents and photocatalysis.
引用
收藏
页码:210 / 225
页数:16
相关论文
共 117 条
[101]   A powerful combination: recent achievements on using TBAI and TBHP as oxidation system [J].
Wu, Xiao-Feng ;
Gong, Jin-Long ;
Qi, Xinxin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (31) :5807-5817
[102]   THE P53 MDM-2 AUTOREGULATORY FEEDBACK LOOP [J].
WU, XW ;
BAYLE, JH ;
OLSON, D ;
LEVINE, AJ .
GENES & DEVELOPMENT, 1993, 7 (7A) :1126-1132
[103]   Synthesis of novel dispiro [1-benzothiophene-5,3′-pyrrolidine-2′,3"'-indole] derivatives via 1,3-dipolar cycloaddition of azomethine ylide [J].
Yan, Jinlong .
JOURNAL OF CHEMICAL RESEARCH, 2014, (01) :50-53
[104]   Recent Advances in Green Synthesis of 3,3′-Spirooxindoles via Isatin-based One-pot Multicomponent Cascade Reactions in Aqueous Medium [J].
Yan, Li-Jun ;
Wang, Yong-Chao .
CHEMISTRYSELECT, 2016, 1 (21) :6948-6960
[105]   Unprecedented formation of spiro[indoline-3,7′-pyrrolo[1,2-a]azepine] from multicomponent reaction of L-proline, isatin and but-2-ynedioate [J].
Yang, Fan ;
Sun, Jing ;
Gao, Hong ;
Yan, Chao-Guo .
RSC ADVANCES, 2015, 5 (41) :32786-32794
[106]   Therapeutic Potential of Spirooxindoles as Antiviral Agents [J].
Ye, Na ;
Chen, Haiying ;
Wold, Eric A. ;
Shi, Pei-Yong ;
Zhou, Jia .
ACS INFECTIOUS DISEASES, 2016, 2 (06) :382-392
[107]   Spirotetrahydro β-Carbolines (Spiroindolones): A New Class of Potent and Orally Efficacious Compounds for the Treatment of Malaria [J].
Yeung, Bryan K. S. ;
Zou, Bin ;
Rottmann, Matthias ;
Lakshminarayana, Suresh B. ;
Ang, Shi Hua ;
Leong, Seh Yong ;
Tan, Jocelyn ;
Wong, Josephine ;
Keller-Maerki, Sonja ;
Fischli, Christoph ;
Goh, Anne ;
Schmitt, Esther K. ;
Krastel, Philipp ;
Francotte, Eric ;
Kuhen, Kelli ;
Plouffe, David ;
Henson, Kerstin ;
Wagner, Trixie ;
Winzeler, Elizabeth A. ;
Petersen, Frank ;
Brun, Reto ;
Dartois, Veronique ;
Diagana, Thierry T. ;
Keller, Thomas H. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (14) :5155-5164
[108]   Spirooxindoles: Promising scaffolds for anticancer agents [J].
Yu, Bin ;
Yu, De-Quan ;
Liu, Hong-Min .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 :673-698
[109]   Green synthesis of Au-Pd bimetallic nanoparticles: Single-step bioreduction method with plant extract [J].
Zhan, Guowu ;
Huang, Jiale ;
Du, Mingming ;
Abdul-Rauf, Ibrahim ;
Ma, Yao ;
Li, Qingbiao .
MATERIALS LETTERS, 2011, 65 (19-20) :2989-2991
[110]   Iodine-promoted three-component reaction for the synthesis of spirooxindoles [J].
Zhang, Min ;
Yang, Wenbo ;
Qian, Min ;
Zhao, Ting ;
Yang, Liuqing ;
Zhu, Chunyin .
TETRAHEDRON, 2018, 74 (09) :955-961