Metal-Catalyzed Conia-ene Reaction And Tandem Reaction Leading To Oxindoles

The five-membered ring and six-membered ring structures exists in many nature products and pharmaceutical intermediates. Many important methods for constructing five-membered ring and six-membered ring structures have been developed, including Lewis acid-catalyzed Conia-ene reaction and transition metal-catalyzed Tandem reaction. Oxindoles were widely existing in bioactive ring compounds and natural products. The dissertation mainly described the efficient and high regioselective synthesis of five to six-membered rings by Lewis acid-catalyzed Conia-ene reaction, and synthesis of Oxindoles by C-S cleavage/carbopalladation Tandem reaction using 3-(diphenylmethylene)-1-alkylindolin-2-one and 1,2-bis(phenylsulfonyl)ethane as the reaction partner.1. An inexpensive, efficient and regionselective ZnCl2-catalyzed Conia-ene intramolecular reaction was presented. The ZnCl2/Yb(OTf)3 catalytic system was suitable for a various ofβ-alkynic 1,3-dicarbonyl compounds. In the presence of ZnCl2 and Yb(OTf)3, a series ofβ-alkynic 1,3-dicarbonyl compounds were cyclized smoothly to construct five to six-member rings in moderate to good yields.2. A novel and selective protocol has been developed for the synthesis of 3-(diphenylmethylene)-1-alkylindolin-2-ones by a palladium-catalyzed intramolecular tandem reactions of N-(2-iodophenyl)-N-alkyl-3-phenylpropiolamide. In the present of Pd(TFA)2, DMEDA, KHCO3 and air, a variety of N-(2-iodophenyl)-N-alkyl-3-phenylpropiol-amide underwent the reaction with 1,2-bis(phenylsulfonyl)ethane to afford the corresponding oxindols in moderate to good yields.