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Efficient Synthesis Of Quinolines,Alcohols And Amides Through Br(?)nsted Acid Catalysis Or Cooperative Catalysis Of Copper,Silver And Br(?)nsted Acid

Posted on:2020-05-24Degree:DoctorType:Dissertation
Country:ChinaCandidate:Waqar AhmedFull Text:PDF
GTID:1361330572990346Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
The strategies for efficient organic synthesis with environmentally benign reagents.solvents and catalysts have attracted considerable attention.The modern academia and industry aim at the chemical reactions that utilize simple reaction set up with easily available and stable feedstock like alkenes,alkynes,amines,and alcohols.In the second chapter of this dissertation,the metal-and solvent-free synthesis of quinolines from simple alkynes or alkenes and N-alkylanilines has been described.The reactions of terminal alkynes with N-alkylanilines proceeded smoothly in the presence of trifluoromethanesulfonic acid(TfOH.15 mol%)and oxygen as the catalyst and oxidant,respectively,to afford the quinoline products in 68%-92%yields.Similarly,the reactions of arylalkenes with N-alkylanilines proceeded also smoothly under the same reaction conditions to provide quinoline products in 61%-89%yields.The functional groups like Br,Cl,Me,and OCOMe linked on N-alkylaniline moiety were found compatible with reaction conditions.Similarly the functional groups like Cl,F,Me,OMe,and OCOMe linked on alkynes or alkenes remained intact.The direct allylative carbohydroxylation of arylalkenes with allylic alcohols through cooperative catalysis of copper.silver,and Bronsted acid has been described in the third chapter of this dissertation.The reactions of various allyl alcohols having F,Cl,Br,alkyl,and acetyl groups with arylalkenes bearing F.Cl,Br,alkyl,and CICH2 groups proceeded smoothly to form the carbohydroxylation products in 50%-88%yields.The synthetically useful functional groups,such as Cl,Br,acetyl,and CICH2,remained intact during the functionalization reaction.This is the first example of allyl and hydroxyl group addition to alkenes with good control of regioselectivity under cooperative catalysis of copper,silver and Bronsted acid,The three component carboamination reaction of arylalkenes.allyl alcohols,and nitriles proceeded through cooperative catalysis of copper,silver,and Bronsted acid has been discussed in the fourth chapter of this dissertation.Various allyl alcohols and arylalkenes were found to be well compatible and provided desired carboamination products in 56%-88%yields.Functional groups like F,Cl.Br.and alkyl remained intact during the carboamination reaction.Both aromatic nitriles bearing F,Cl,Br,and Me groups on benzene rings and aliphatic nitriles could be used for this type of carboamination reaction.This is the first example of carboamination of alkenes with readily available allyl alcohols and nitriles.
Keywords/Search Tags:Quinoline, Carbohydroxylation, Carboamination, Cooperative Catalysis
PDF Full Text Request
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