An Efficient Synthesis of Novel Dispirooxindole Derivatives via One-Pot Three-Component 1,3-Dipolar Cycloaddition Reactions

doi:10.3390/molecules171112704

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Molecules 2012, 17(11), 12704-12717; doi:10.3390/molecules171112704

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An Efficient Synthesis of Novel Dispirooxindole Derivatives via One-Pot Three-Component 1,3-Dipolar Cycloaddition Reactions

Zhibin Huang^1,†, Qian Zhao^2,†, Gang Chen³, Huiyuan Wang¹, Wei Lin¹, Lexing Xu⁴, Hongtao Liu⁴, Juxian Wang⁴, Daqing Shi^1,* and Yucheng Wang^4,*

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China ² Tianjin ShuiGe Hospital, Tianjin 300120, China ³ Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory, Xinchang 312500, China ⁴ 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

(This article belongs to the Section Organic Synthesis)

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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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Cite This Article

MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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