Study On N-H Functionalization Of 3-Cyanoindole And Pyrazole

Indoles and pyrazoles have good biological activities,and play a prominent role in the field of medicine,especially in the treatment of cancer.Synthesis of N1-position substituted indole and pyrazole compounds often need Pt or its complex as a catalyst,which not only the price is more expensive,but also the harm to the environment is relatively large.Aza-Michael reaction is often used to construct C?N bond and to synthesize ?-aminocarbonyl compounds in organic synthesis.The method is simple and atomic economic.MBH adducts have the characteristics of multifunctional groups,in the reaction process,which can be used not only as alkenes but also as Michael receptors.It was found that the aza-Michael reaction of indole with ?,?-unsaturated ketones at N1-position has not been reported.In addition,although many reactions between MBH adducts and various nucleophiles have been documented,the synthesis of N1-substituted pyrazole by the reaction of pyrazole with MBH has not been reported.Here,the aza-Michael reaction of 3-cyanoindole with ?,?-unsaturated ketones and the allylation of pyrazole with MBH adducts were studied,and good experimental results were obtained.The thesis is divided into two parts,a total of four chapters.Part I: Study on the Aza-Michael Reaction of Indoles with ?,?-Unsaturated KetonesChapter 1: Application of Indoles and Advances in Aza-Michael Reactions of IndolesIn this chapter,we introduced the application of indole compounds in medicine,pigment and agriculture,and summarized the aza-Michael reaction of indoles from both aspects of intramolecular and intermolecular reactions.Chapter 2: Study on the Aza-Michael Reaction of 3-Cyanoindole with ?,?-Unsaturated KetonesBased on the experimental investigation,we have developed a new method for the aza-Michael reaction of 3-cyanoindole with ?,?-unsaturated ketones in the presence of KOH.The method has the advantages of mild reaction conditions,easy operation and wide scope of substrate.Part 2: Study on the Reaction of Pyrazole with MBH AdductsChapter 3: Application of Pyrazole Compounds and Advance in the Reaction of MBH AdductsIn this chapter,we emphatically introduced the application of pyrazole compounds in pharmaceutical,pesticide and industry.The reactions of MBH acetates,MBH carbonates and MBH alcohols at ??-position with different nucleophiles were reviewed.Chapter 4: Study on the N-SN2' Reaction of Pyrazole with MBH CarbonatesAfter a systematic study,we have developed a new method for the catalytic allylation of pyrazole and MBH carbonates with a relatively green,inexpensive catalyst.The target product contains a variety of functional groups,which can be further transformed.This contributes to the diversity synthesis of N1-substituted pyrazole compounds.