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Molecules 2016, 21(9), 1113; doi:10.3390/molecules21091113

Efficient Synthesis of Fully Substituted Pyrrolidine-Fused 3-Spirooxindoles via 1,3-Dipolar Cycloaddition of Aziridine and 3-Ylideneoxindole

1,†
,
2,†
,
2
,
2
,
1,* and 2,*
1
Key Laboratory of Drug Targeting and Drug Delivery Systems of Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China
2
State Key Laboratory Breeding Base of Systematic Research, Development and Utilization of Chinese Medicine, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Mark A. Rizzacasa
Received: 26 July 2016 / Revised: 12 August 2016 / Accepted: 18 August 2016 / Published: 24 August 2016
(This article belongs to the Special Issue Pericyclic Reactions)
View Full-Text   |   Download PDF [1465 KB, uploaded 24 August 2016]   |  

Abstract

Drug-like spirocyclic scaffolds have been prepared by fusing fully functionalized pyrrolidine with oxindoles in an approach based on 1,3-dipolar cycloaddition. Reaction between aziridine and 3-ylideneoxindole generated diverse spirooxindole-pyrrolidines in good yield (up to 95%) with high diastereoselectivity (up to >20:1). The reaction also proceeded smoothly with several other synthetically useful activated trisubstituted olefins. The mild reaction conditions, short reaction times, and high tolerance for various substitutions make this approach attractive for constructing pharmacologically interesting spiro-architectures. View Full-Text
Keywords: spirooxindole-pyrrolidine; 1,3-dipolar cycloaddition; aziridine; single-step reaction spirooxindole-pyrrolidine; 1,3-dipolar cycloaddition; aziridine; single-step reaction
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Ren, W.; Zhao, Q.; Zheng, C.; Zhao, Q.; Guo, L.; Huang, W. Efficient Synthesis of Fully Substituted Pyrrolidine-Fused 3-Spirooxindoles via 1,3-Dipolar Cycloaddition of Aziridine and 3-Ylideneoxindole. Molecules 2016, 21, 1113.

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