Thermal-mediated catalyst-free heterolytic cleavage of 3-halooxindoles: rapid access to 3-functionalized-2-oxindoles
Literature Information
Publication Date
2018-12-05
DOI
10.1039/C8QO01222A
Impact Factor
5.281
Authors
Jing Yue, Shuang Chen, Huan-Huan Liu, Kai-Mo Yang, Ting-Ting Feng, Ying Zhou
View Original
Abstract
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
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