| 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
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| 通讯作者 | Chen, G (reprint author), Xian Shiyou Univ, Coll Chem & Chem Engn, Xian 710065, Shaanxi, Peoples R China. ; gangchen@xsyu.edu.cn ; haoxj@mail.kib.ac.cn |
| 2013-07-01 | |
| 发表期刊 | RESEARCH ON CHEMICAL INTERMEDIATES
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| ISSN | 0922-6168 |
| 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] |
| 学科领域 | Chemistry ; Multidisciplinary |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000320559100016 |
| 引用统计 | |
| 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 |
| 推荐引用方式 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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