Study On The Reaction Based On N-alkyl-4-piperidone

Aliphatic tertiary amines are a key type of organic groups widely presented in organic molecules.Due to the high bond energy of C-N bonds of aliphatic tertiary amines,the use of C-N bond cleavage reactions of aliphatic tertiary amines to provide carbon or nitrogen sources for the synthesis of compounds is difficult and challenging.In recent years,metal-free protocols for C-N bond activation,especially via electron transfer complexes(EDA complexes)formation,has become a hot research topic.In this thesis,carbon-nitrogen bonds in cyclic tertiary amines are cleaved by means of forming electron transfer complexes formation and some valuable organic compounds are thus prepared.This thesis consists three chapters:Chapter 1: Research progress on carbon-nitrogen bond cleavage reactions of aminesThis chapter mainly introduces the different activation methods of carbon-nitrogen bond activation of amine compounds,some examples of the application of carbon-nitrogen bond cleavage reaction in organic synthesis are organized and the activation methods in various methods are discussed.Chapter 2: Study on the Sulfonation of N-Alkyl-4-oxopipidinium Salts via C-N Bond CleavageIn this chapter,the sulfonylation of N-alkyl-4-oxopiperidinium salts was discussed in detail.The possible reaction mechanism is: First,the sulfonyl chloride and N-methylmorpholine formed a charge transfer complex through partial charge transfer.The S-Cl bond of the sulfonyl chloride was then cleaved to generate a sulfonyl radical and a chlorine radical.Second,the sulfonyl radical and the chlorine radical further induce the double C-N bond cleavage of the N-alkyl-4-oxoperidinium salt to generated a secondary amine that is captured by the sulfonyl chloride to form the desired sulfonamide product.By this method,that is,under metal-and oxidant-free condition,two C-N bonds in 4-oxopiperidine ring is broken in one step.Chapter 3: Oxidative Coupling of Hydroquinone with N-Alkyl-4-piperidoneThis chapter mainly studies the coupling reaction between 1,4-hydroquinoneand N-alkyl-4-piperidone under the oxidation of iodobenzenediethyl ester.It was found that poly-substituted 1,4-hydroquinone can be effectively oxidatively coupled with N-alkyl-4-piperidone under weakly acidic conditions and a polycyclic compound was formed.