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Cascade arylalkylation of activated alkenes: synthesis of chloro- and cyano-containing oxindoles.
J Org Chem. 2015 Mar 06; 80(5):2621-6.JO

Abstract

The general method for the oxidative cyclization of arylacrylamides with dichloromethane or acetonitrile has been developed. The reactions described provide novel access to chloro- and cyano-containing oxindoles in good to moderate yields that allow the direct formation of a C-C bond and the construction of an oxindole ring in one reaction. The use of a cheap and easily prepared Mn(OAc)3 represents an added advantage of this method.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li X
Department of Chemistry, College of Chemistry and Chemical Engineering, and Key Laboratory for Chemical Biology of Fujian Province, Xiamen University , Xiamen, Fujian 361005, China.
Xu J
No affiliation info available
Gao Y
No affiliation info available
Fang H
No affiliation info available
Tang G
No affiliation info available
Zhao Y
No affiliation info available

MeSH

AcetatesAcetonitrilesAlkenesCatalysisCyclizationIndolesMolecular StructureOrganometallic CompoundsOxidation-ReductionOxindolesSpiro Compounds

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25658775

Citation

Li, Xueqin, et al. "Cascade Arylalkylation of Activated Alkenes: Synthesis of Chloro- and Cyano-containing Oxindoles." The Journal of Organic Chemistry, vol. 80, no. 5, 2015, pp. 2621-6.
Li X, Xu J, Gao Y, et al. Cascade arylalkylation of activated alkenes: synthesis of chloro- and cyano-containing oxindoles. J Org Chem. 2015;80(5):2621-6.
Li, X., Xu, J., Gao, Y., Fang, H., Tang, G., & Zhao, Y. (2015). Cascade arylalkylation of activated alkenes: synthesis of chloro- and cyano-containing oxindoles. The Journal of Organic Chemistry, 80(5), 2621-6. https://doi.org/10.1021/jo502777b
Li X, et al. Cascade Arylalkylation of Activated Alkenes: Synthesis of Chloro- and Cyano-containing Oxindoles. J Org Chem. 2015 Mar 6;80(5):2621-6. PubMed PMID: 25658775.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cascade arylalkylation of activated alkenes: synthesis of chloro- and cyano-containing oxindoles. AU - Li,Xueqin, AU - Xu,Jian, AU - Gao,Yuzhen, AU - Fang,Hua, AU - Tang,Guo, AU - Zhao,Yufen, Y1 - 2015/02/16/ PY - 2015/2/7/entrez PY - 2015/2/7/pubmed PY - 2015/10/16/medline SP - 2621 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 80 IS - 5 N2 - The general method for the oxidative cyclization of arylacrylamides with dichloromethane or acetonitrile has been developed. The reactions described provide novel access to chloro- and cyano-containing oxindoles in good to moderate yields that allow the direct formation of a C-C bond and the construction of an oxindole ring in one reaction. The use of a cheap and easily prepared Mn(OAc)3 represents an added advantage of this method. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/25658775/Cascade_arylalkylation_of_activated_alkenes:_synthesis_of_chloro__and_cyano_containing_oxindoles_ DB - PRIME DP - Unbound Medicine ER -