Synthesis Of Heterocycles Such As Spiro, Bisindoles And Naphthalene By Annulation Of Alkynes

The dissertation concerns about three parts : (1) selective synthesis of spiro[4,5]trienyl esters via an intramolecular electrophilic ipso-iodocyclization; (2) the synthesis of bis(indolyl)methanes by Silver-catalyzed tandem reaction of o-ethynylanilines with aryl aldehyde; (3) ZnI2-Catalyzed benzannulation of o-alkynylbenzaldehydes with alkenes leading to 1-acyl-2-substitutednaphthalenes. The main contents of dissertation are summarized as follow:(1) Recent advances in the synthesis of heterocyclic compounds via cyclization reaction are introduced.(2) Synthesis of spiro compounds via iodocyclization was described. We successfully prepared spiro[4,5]trienyl acetates by intramolecular iodocyclization. The reaction is easy to operate and environment friendly. The reaction are tolerated a wide range of substrates.(3) Synthesis of bisindole via silver-catalyzed tanden has been developed. In the presence of AgNO3, 2-ethynylaniline reacted with benzaldehyde to afford the corresponding bisindole compounds in high yield in short reaction time.(4) We have discovered a novel and efficient method for the synthesis of 1-acyl-2-arylnaphthalenes via ZnI2-catalyzed between o-alkynylbenzenes and alkenes. In the presence of ZnI2 and p-quinone, a variety of o-alkynylbenzaldehyde and successfully underwent the tandem reaction with arylethenes to selectively prepare 1-acyl-2-arylnaphthalenes in moderate to good yields. The presented tandem benzannulation-dehydrogenation reactions represented a facile route for the generation of naphthalenes.