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Transition Metal-Catalyzed Synthesis of N-Fused Heterocycles

Author: LuJuYou
Tutor: FuHua
School: Tsinghua University
Course: Chemistry
Keywords: transition metal-catalyzed cross-coupling N-fused heterocycles C-H amination synthetic method
CLC: O626
Type: PhD thesis
Year: 2013
Downloads: 32
Quote: 0
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Abstract


N-Heterocycles are ubiquitous in a variety of natural products and biologicallyactive molecules, and they play important roles in the pharmaceutical and agrochemicalindustries. The development of transition metal-catalyzed cross-coupling reactions forthe formation of heterocycles continues to be an active area of research. Recently, thedirect functionalization of C-H bonds has made great progress. Their application on theconstruction of N-heterocycles has been reported. In this dissertation, new transitionmetal-catalyzed methods have been developed for synthesis of N-fused heterocycles,and some important results were obtained.A simple and efficient copper-catalyzed one-pot tandem method has beendeveloped for synthesis of benzimidazo[1,2-b]isoquinolin-11-one derivatives. Theprotocol used cheap CuCl as the catalyst, readily available substituted2-halo-N-（2-halophenyl）benzamides and alkyl2-cyanoacetates or malononitrile as thestarting materials. The couplings of substituted2-halo-N-（2-halophenyl）benzamideswith alkyl2-cyanoacetates or malononitrile were performed well under mild conditionswithout addition of any ligand or additive, and the correspondingbenzimidazo[1,2-b]isoquinolin-11-ones were obtained in good to excellent yields. Thepresent method shows economical, practical and starting material readily availableadvantages over the previous methods, so it will provide a new strategy for constructionof diverse and useful N-fused heterocyclic compounds for organic chemistry andmedicinal chemistry.A convenient and efficient copper-catalyzed cascade method has been developedfor synthesis of benzimidazoisoquinoline derivatives. The protocol used inexpensiveCuI as the catalyst, readily available substituted2-（2-halophenyl）benzoimidazoles andalkyl cyanoacetates as the starting materials, and the corresponding alkyl6-aminobenzimidazo[2,1-a]isoquinoline-5-carboxylates were obtained in good toexcellent yields. The novel method provides diverse and useful N-fused heterocycles forcombinatorial chemistry and medicinal chemistry.A convenient and efficient palladium-catalyzed synthesis of aromatic ketones andisoindolobenzimidazoles has been developed via selective aromatic C-H bond acylation. The protocol used Pd（OAc）2as the catalyst, readily available carboxylic acids as theacylating reagents,（CF3CO）2O as the activated agent of the acids, and thecorresponding aromatic ketones and isoindolobenzimidazoles were obtained in good toexcellent yields. The novel and practical method provides a new and useful strategy forsynthesis of aromatic ketones and isoindolobenzimidazoles.An efficient copper-catalyzed aerobic oxidative intramolecular alkene C-Hamination leading to N-heterocycles has been developed. The protocol used cheap andreadily available Cu（O2CCF3）2as the catalyst, substituted3-benzylidene-2-pyridin-2-ylmethyl-2,3-dihydro-isoindol-1-ones as the startingmaterials, economical and environment friendly air as the oxidant, and thecorresponding N-heterocycles were obtained in good to excellent yields. This methodshould provide a new and useful strategy for constructing N-fused heterocycles.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Heterocyclic compounds
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