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Isatin-Based Study On The Clean Synthesis Of Pyrazole Spirooxindole Derivatives

Posted on:2018-07-07Degree:MasterType:Thesis
Country:ChinaCandidate:Z S WangFull Text:PDF
GTID:2321330536957176Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
In this paper,several series of spiro compounds were synthesized on the basis of multicomponent reaction.This study has the advantages of easily available raw materials,low price and simple reaction operation.In this paper,the multicomponent reactions were operated in the water.This is the effient process for the synthesis of diversity of molecules.The other advantages of this study are high polymerizability,high economic efficiency and environmental friendliness.The first chapter mainly introduces the meaning,history and merits of the multicomponent reaction,the significance and application prospect of synthetic spiro compounds,and introduces the research progress of various spiro compounds at the 3-position based on the raw materials.The application of organic synthesis in water in recent years is briefly described.In the second chapter,a series of pyrazolopyridine spirooxindole derivatives were synthesized by using 3-amino-1-phenyl-1H-pyrazol-5(4H)-one,isatins and diacetophenones in water used acetic acid as catalyst.Avoiding the use of organic solvents,it is in accordance with the concept of "green chemistry"In the third chapter,the indane and naphthyl ketones,isatins and 3-amino-1-phenyl-1H-pyrazol-5(4H)-one were used to synthesize indene heterocyclic and benzoquinoline spirooxindole derivatives,and this synthesis enriched these compound libraries.In the fourth chapter,a series of spirooxidized indole derivatives containing pyrazole ring were synthesized by using isatins,3-amino-1-phenyl-1H-pyrazol-5(4H)-one and monocyclic ketones or heterocyclic ketones as raw materials in aqueous and acetic medium.The advantages of this reaction are mild reaction conditions,simple operation and high yields.In the fifth chapter,an efficient and green reaction of isatins,3-amine-1H-pyrazole and 1,3-diketone in aqueous medium was reported to obtain the pyrazoloquinoline and pyrazolopyridine,and pyrazolopyridine compounds.A fast,simple,economical,environmentally friendly synthetic pathway was provided in this stnthesis.All products’ structures were characterized by NMR,IR and HRMS.The possible reaction mechanisms were proposed for all the gaining compounds.Experimental studies have shown that multi-component reactions and aqueous medium were the efficient conditions for the synthesis of spirooxindole compounds,Moreover,isatin is vital reagent for the synthesis of spiro compounds.This study has the advantages of high atom economy,no toxicity,environment friendliness,mild condition and high yield.
Keywords/Search Tags:spiro compounds, isatin, multicomponent reaction, acetic acid, water
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