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Transtion-metal Catalyzed Arylation Of1H-indoles And Construction Of N-containing Heterocyclic Or Carbocyclic Compounds

Posted on:2015-12-05Degree:DoctorType:Dissertation
Country:ChinaCandidate:Y X ChenFull Text:PDF
GTID:1221330428998883Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Transition-metal catalyzed reactions represent important and useful synthetic methods in organic synthesis, which have widely applications in medicinal chemistry and materials science. During the last decade, those reactions have received increasing attention especially for the construction of C-C or C-N bonds and cyclization reactions. The main focus of this thesis has been on transtion-metal-catalyzed formation of C-C/N bonds and cyclization reactions through three sections. The results are below:1. The methods and development of arylation of indoles and various arylating reagents were introduced. Based on those reviews, a novel Pd(OAc)2-catalyzed approach to direct C3-arylation of1H-indoles with arylhydrazines as arylating reagents has been developed. The procedure, using air as the oxidant, is a simple, economical, and environmentally friendly protocol, which could be applied to various available substrates in moderate to good yields.2. The methods and development for synthesis of quinoxalines were introduced. Based on those reviews, an easy and efficient CuBr2-catalyzed reaction for the synthesis of quinoxalines from o-phenylenediamines and nitroolefins using ethanol as solvent has been developed. This reaction could proceed well without additional base and be applied to various available substrates in moderate to good yields with NO2group as the terminal oxidant. The procedure is a simple, economical, and environmentally friendly protocol for the synthesis of quinoxalines.3. The methods and development for synthesis of indenes and the direct functional ization of benzylic compounds were introduced. Based on those reviews, a novel approach to synthesizing multi-substituted indenes by FeCl2-catalyzed domino-reaction of benzylic compounds and alkynes under mild conditions was developed. This system could be applied to various available substrates with a one-step synthetic procedure in moderate to good yields.
Keywords/Search Tags:C-H Activation, 1H-Indoles, Arylhydrazines, Quinoxaline, Nitroolefins, Indene, Benzylic compounds
PDF Full Text Request
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