Synthesis Of Spirooxindoles Based On Oxyarylative Difunctionalization Of Furans And Indoles

Furan and indole as two kinds of important aromatic compounds are easily obtained from natural products.Due to their low aromaticity energy,various methods and applications involving dearomatization of furan and indoles for the synthesis of structurally complex compounds have been reported.Despite extensive efforts,the construction of bioactive heterocyclic compound by dearomatization of furan and indole with efficient process is still worth paying attention.Spirooxindolones compounds are structural motifs frequently founded in natural products,pharmaceuticals,agrochemicals,and functional materials.Palladiumcatalyzed carbon-carbon or carbon-heteroatom bonds formation serves as one important process in organic chemistry.In this context,we have studied the Pd-catalyzed arylalkoxyation of furan and indole access to spirooxindolones compounds with potential bioactivity.In the first chapter,we have introduced the bifunctional reaction of N-arylolefins,furan,benzofuran,and indole,the biological activity of spirooxindoles and the methods for synthesis of it.In the second chapter,we have discovered a novel palladium-catalyzed dearomatizing 2,5-arylalkoxylation of furan rings,which provided convenient,diastereospecific access to structurally novel spirooxindoles.This protocol involves an intramolecular dearomatizing Heck-type ?-arylation of the furan ring to produce a cyclic allylic palladium and the subsequent intermolecular introduction of an alkyloxyl group at the other ?-position of the ring,with hight diastereoselectivity.In the third chapter,we have developed regio-selective intramolecular direct C-3 and C-2 arylations of the indole rings of N-(o-bromophenyl)-3-indolecarboxamides to produce disasterospecificspiro-indoline-3,3'-oxindoles and 5,11-dihydro-6H-indolo [3,2-c]quinolin-6-ones under different reaction conditions.