Thermal-mediated catalyst-free heterolytic cleavage of 3-halooxindoles: rapid access to 3-functionalized-2-oxindoles

文献情報

出版日 2018-12-05

DOI 10.1039/C8QO01222A

インパクトファクター 5.281

著者

Jing Yue, Shuang Chen, Huan-Huan Liu, Kai-Mo Yang, Ting-Ting Feng, Ying Zhou

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要旨

Herein a previously unreported catalyst-free SN1 reaction of the 3-halooxindoles to build 3-functionalized-2-oxindoles is described. The present protocol utilizes the thermal-mediated heterolytic cleavage of the 3-halooxindoles to generate a highly electrophilic 1-H-o-azaxylylene-1-ium A or 1-alkyl-o-azaxylylene-1-ium B intermediate as the Michael acceptor, avoiding the utilization of an additional base and metal as promoters, and providing a diversity-oriented approach to a series of 3-functionalized-2-oxindoles bearing a tetrasubstituted center in high yields (up to 93% yield). This method could provide libraries of structurally diverse and medicinally important small molecules that could aid the search for new bioactive molecules.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Thermal-mediated catalyst-free heterolytic cleavage of 3-halooxindoles: rapid access to 3-functionalized-2-oxindoles

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