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An Efficient Synthesis of Novel Dispirooxindole Derivatives via One-Pot Three-Component 1,3-Dipolar Cycloaddition Reactions
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
Tianjin ShuiGe Hospital, Tianjin 300120, China
Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory, Xinchang 312500, China
Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 4 September 2012; in revised form: 16 October 2012 / Accepted: 18 October 2012 / Published: 26 October 2012
Abstract: A series of novel dispirooxindoles have been synthesized through three-component 1,3-dipolar cycloaddition of azomethine ylides generated in situ by the decarboxylative condensation of isatin and an α-amino acid with the dipolarophile 5-benzylidene-1,3-dimethylpyrimidine-2,4,6-trione. This method has the advantages of mild reaction conditions, high atom economy, excellent yields, and high regio- and stereo-selectivity.
Keywords: dispirooxindole; three-component reaction; 1,3-dipolar cycloaddition; azomethine ylide
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Huang, Z.; Zhao, Q.; Chen, G.; Wang, H.; Lin, W.; Xu, L.; Liu, H.; Wang, J.; Shi, D.; Wang, Y. An Efficient Synthesis of Novel Dispirooxindole Derivatives via One-Pot Three-Component 1,3-Dipolar Cycloaddition Reactions. Molecules 2012, 17, 12704-12717.
Huang Z, Zhao Q, Chen G, Wang H, Lin W, Xu L, Liu H, Wang J, Shi D, Wang Y. An Efficient Synthesis of Novel Dispirooxindole Derivatives via One-Pot Three-Component 1,3-Dipolar Cycloaddition Reactions. Molecules. 2012; 17(11):12704-12717.
Huang, Zhibin; Zhao, Qian; Chen, Gang; Wang, Huiyuan; Lin, Wei; Xu, Lexing; Liu, Hongtao; Wang, Juxian; Shi, Daqing; Wang, Yucheng. 2012. "An Efficient Synthesis of Novel Dispirooxindole Derivatives via One-Pot Three-Component 1,3-Dipolar Cycloaddition Reactions." Molecules 17, no. 11: 12704-12717.