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
Corresponding AuthorChen, 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
Source PublicationRESEARCH ON CHEMICAL INTERMEDIATES
ISSN0922-6168
Volume39Issue:6Pages:2445-2450
AbstractThe 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.
KeywordHuisgen Reaction Regioselectivity Regioisomer Spiro [Pyrrolidine-2 3 '-oxindole]
Subject AreaChemistry ; Multidisciplinary
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000320559100016
Citation statistics
Cited Times:12[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/16829
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.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
Recommended Citation
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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