Studies On The Tandem Reactions That Involved Secondary Alcohols Promoted By Lewis Acids And Protonic Acids

This thesis deals with the tandem reactions that involved secondary alcohols promoted by lewis acids and protonic acids. It is divided into two chapters.Chapter1:Chapter1briefly introduces the multicomponent cyclization reactions, tandem cyclization reactions and disproportionation reactions that involved alcohols, meanwhile showed some applications and the latest progress of these reactions.Chapter2:Chapter2contains three parts of my work,(1) one-pot synthesis of pyrrolidino-and piperidinoquinolinones by three-component aza-Diels-Alder reactions of in situ generated N-arylimines and cyclic enamides. An efficient method for synthesis of hexahydropyrrolo[3,2-c]quinolin2-ones and hexahydropyridino[3,2-c]quinolin-2-ones by one-pot two-step aza-Diels-Alder reactions of N-arylimines, produced in situ by the condensation of anilines and benzaldehydes, with the cyclic enamides, produced in situ from BF3·OEt2promoted dehydration of5-hydroxypyrrolidin-2-ones and6-hydroxypiperidin-2-ones. The reaction afforded the hexahydropyrrolo[3,2-c]quinolin-2-ones as a single exo-diastereomer in most cases and afforded the hexahydropyridino[3,2-c]quinolin-2-ones as a mixture of endo-and exo-isomers favoring the endo-diastereomer.(2) one-pot synthesis of indene derivatives by CF3SO3H-promoted reactions of benzylic alcohols and1,3-dicarbonyl compounds. This reaction affords the indene derivates in moderate to high yield. For the reactions of methoxy-or methyl-substituted diarylmethanols with1,3-dicarbonyls,2equiv TfOH were needed to reach the best results, but for the reactions of methoxy-substituted arylethanols with1,3-dicarbonyls,0.6equiv TfOH at lower temperatures were capable to promote the reaction finished.(3) p-toluene sulfonic acid promoted the disproportionation reactions of alcohols (3-hydroxyisoindol-1-ones) under microwave. We successfully studied the disproportionation reaction of N-substituted-3-hydroxyisoindolin-1-ones, also the disproportionation reactions of2-carboxybenzaldehyde and amines. This method provided a new way to synthesis isoindolinl-1-ones.