title: Efficient Synthesis of Fully Substituted Pyrrolidine-Fused 3-Spirooxindoles via 1,3-Dipolar Cycloaddition of Aziridine and 3-Ylideneoxindole.
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.
authors: 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. sklb_renwen@126.com.
authors: Wen
authors: W
authors: Ren
authors: 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. zhaoqianjy@126.com.
authors: Qian
authors: Q
authors: Zhao
authors: 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. zhengchuan@cdutcm.edu.cn.
authors: Chuan
authors: C
authors: Zheng
authors: 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. zhaoqiongl@126.com.
authors: Qiong
authors: Q
authors: Zhao
authors: 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. guoli@scu.edu.cn.
authors: Li
authors: L
authors: Guo
authors: 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. huangwei@cdutcm.edu.cn.
authors: Wei
authors: W
authors: Huang
mesh_terms: D001388:Aziridines / Q000737:chemistry; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001388:Aziridines; D013141:Spiro Compounds; C033132:aziridine
keywords: 1,3-dipolar cycloaddition; aziridine; single-step reaction; spirooxindole-pyrrolidine