Facile Synthesis of Functionalized Spiropyrrolizidine Oxindoles via a？Three-Component Tandem Cycloaddition Reaction.docVIP

Molecules 2011, 16, 8745-8757; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Facile Synthesis of Functionalized Spiropyrrolizidine Oxindoles via a Three-Component Tandem Cycloaddition Reaction Yong-Mei Xie 1, Yu-Qin Yao 1, Hong-Bao Sun 1, Ting-Ting Yan 1, Jie Liu 1,* and Tai-Ran Kang 2,* 1 State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Chengdu, 610041, China; E-Mails: xieym@ (Y.M.X.); yuqin_yao@163.com (Y.Q.Y.); 773770248@ (H.B.S.); 121968698@ (T.T.Y.) 2 Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong, 637002, China * Authors to whom correspondence should be addressed; E-Mails: liujie2011@ (J.L.); kangtairan@ (T.R.K.); Tel.: +86-28 Fax: +86-28 Received: 26 August 2011; in revised form: 30 September 2011/ Accepted: 3 October 2011 / Published: 19 October 2011 Abstract: An efficient synthesis of functionalized spiropyrrolizidine oxindoles via a three- component tandem cycloaddition has been achieved. This strategy can provide direct and rapid access to spiropyrrolizidine oxindoles in high yields (up to 99%) with excellent diastereoselectivities (up to 99:1 dr). The features of this procedure are the following: mild reaction conditions, high yields, high diastereoselectivities, one-pot procedure and operational simplicity. Keywords: spiropyrrolizidine oxindoles; cycloaddition; isatin 1. Introduction Spirocyclic oxindoles are valuable synthetic intermediates and constitute the core units of many pharmacological agents and alkaloids [1-3]. These compounds have attracted much attention from synthetic chemists due to their diverse biological activities including antimycobacterial [4-9], antitumor [10-14], antimicrobial [15], antibacterial [16,17], antifungal [18,19],