A Catalyst‐Free Self‐Catalyzed [3+2] Cycloaddition Reaction of 3‐Isothiocyanato Oxindoles and Vinylpyridines. Issue 35 (26th August 2018)

• Record Type: Journal Article
• Authors: Gui, Hou‐Ze; Wei, Yin; Shi, Min
• Is Part Of: European journal of organic chemistry. Issue 35(2018)
• Page Start: 4905
• Page End: 4916
• Publication Date: 2018-08-26
• Subjects: Heterocycles -- Cycloaddition -- Self‐catalyzed reactions -- Mutual activation -- Spiro compounds; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801091
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A catalyst‐free self‐catalyzed [3+2] cycloaddition reaction of 3‐isothiocyanato oxindoles with vinylpyridines has been established, affording the desired products in high yields (up to 97 %) with moderate to good diastereoselectivities (up to 11:1) under mild conditions. The reaction mechanism has been investigated by control experiments, DFT calculations of pK a values and the kinetic studies, revealing that this reaction featured the mutual activation between 3‐isothiocyanato oxindole and vinylpyridine to generate the reactive species. Furthermore, these products could be easily transformed into the corresponding methylated and hydroxylated products under basic conditions. Abstract : We have developed a catalyst‐free self‐catalyzed [3+2] cycloaddition reaction of 3‐isothiocyanato oxindoles with vinylpyridines through mutual activation in good yields.