Investigation of regioselectivity in the synthesis of spiro [pyrrolidine-2,3 '-oxindoles] by use of the Huisgen reaction
Chen, Gang1; Miao, Yan-qing2; Zhou, Rui1; Zhang, Li1; Zhang, Jie1; Hao, Xiao-jiang3
2013-07-01
发表期刊RESEARCH ON CHEMICAL INTERMEDIATES
ISSN0922-6168
卷号39期号:6页码:2445-2450
摘要The Huisgen reaction has been used to synthesize five-membered heterocyclic compounds in high yield and with high regio and stereoselectivity. In the synthesis of spiro [pyrrolidine-2,3'-oxindole] derivatives from isatin, alpha-amino acids, and (E)-beta-phenyl nitroolefins, two regioisomers were obtained in each reaction. The regioselectivity of the major product was found to be different from that in reported work, and was investigated at the B3LYP/6-311G* level of theory. On the basis of this new finding, several conditions, for example molar ratio, solvent, and temperature, which affect the regioselectivity of this reaction were investigated; the results obtained are discussed. It was found that the regioselectivity of this reaction was affected by solvent and temperature, irrespective of the ratio of the reactants. Low temperature and high solvent polarity leads to high regioselectivity, and protic solvents result in higher yield and regioselectivity. These results are of benefit for regioselective synthesis of some compounds.
关键词Huisgen Reaction Regioselectivity Regioisomer Spiro [Pyrrolidine-2 3 '-oxindole]
资助信息Scientific and Technological Plan Projects of Shaanxi Province of China [2012KJXX-40]; Shaanxi Provincial Education Department [12JK0582, 12JK0589]
学科领域Chemistry ; Multidisciplinary
收录类别SCI
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Multidisciplinary
WOS记录号WOS:000320559100016
引用统计
被引频次:9[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/16829
专题植物化学与西部植物资源持续利用国家重点实验室
作者单位1.Xian Shiyou Univ, Coll Chem & Chem Engn, Xian 710065, Shaanxi, Peoples R China
2.Xian Med Univ, Dept Pharmacol, Xian 710068, Shaanxi, Peoples R China
3.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
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GB/T 7714
Chen, Gang,Miao, Yan-qing,Zhou, Rui,et al. Investigation of regioselectivity in the synthesis of spiro [pyrrolidine-2,3 '-oxindoles] by use of the Huisgen reaction[J]. RESEARCH ON CHEMICAL INTERMEDIATES,2013,39(6):2445-2450.
APA Chen, Gang,Miao, Yan-qing,Zhou, Rui,Zhang, Li,Zhang, Jie,&Hao, Xiao-jiang.(2013).Investigation of regioselectivity in the synthesis of spiro [pyrrolidine-2,3 '-oxindoles] by use of the Huisgen reaction.RESEARCH ON CHEMICAL INTERMEDIATES,39(6),2445-2450.
MLA Chen, Gang,et al."Investigation of regioselectivity in the synthesis of spiro [pyrrolidine-2,3 '-oxindoles] by use of the Huisgen reaction".RESEARCH ON CHEMICAL INTERMEDIATES 39.6(2013):2445-2450.
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