N-Alkylation Of Trifluoromethyl Hydrazones And [4+2] Reaction Of O-Aminotrifluoromethyl Acetophenones And Propiolates

Organic fluorine-containing compounds have attracted much attention due to their unique physical and chemical properties and biological activities.Among them,trifluoromethyl compounds are typical fluorine-containing organic compounds,which have been widely used in the fields of medicine,pesticide and material science.At present,there are two main ways to introduce trifluoromethyl group into organic compounds: the first one is to use trifluoromethylation reagents to directly introduce trifluoromethyl group into organic molecules through nucleophilic,electrophilic,and free radical reactions;the second one is to use trifluoromethyl building blocks to synthesize organic compounds containing trifluoromethyl through corresponding chemical reactions.Among the numerous trifluoromethyl building blocks,trifluoromethylated acylhydrazones and o-aminotrifluoromethyl acetophenones play a pivotal role in organic synthesis.This paper reviews the research progress of acylhydrazone compounds in organic synthesis.On this basis,we first synthesized of a series of N-alkyl trifluoromethyl acylhydrazones under mild conditions using trifluoromethyl hydrazones as the trifluoromethyl building block;and then we explored the [4+2] cyclization reaction of o-aminotrifluoromethyl acetophenones and a series of propiolates,and trifluoromethylated 1,4-dihydroquinoline derivatives containing were synthesized,which have potential biological activities.This thesis consists of three chapter:Chapter one: Research progress of acylhydrazone compounds in organic synthesisThis chapter introduces the reactive ability of acylhydrazones and their biological activity;and then summarizes the research progress of acylhydrazone compounds in organic synthesis.Chapter two: Study on N-Alkylation reactions of trifluoromethylated acylhydrazonesN-Alkylation reaction of trifluoromethylated acylhydrazones has been achieved in this chapter.A series of N-alkyl trifluoromethyl acylhydrazones were afforded in good yield.The strategy has advantages of simple and mild reaction conditions,wide scope of substrates and good yields.This protocol provides an efficient and new method for the synthesis of N-alkyl substituted trifluoromethyl acylhydrazones.The N-hydrocarbyl substituted trifluoromethyl hydrazone derivative obtained by this reaction can be used as a new trifluoromethyl synthetic building block in organic synthesis,and is expected to be applied in various fields such as medicine,pesticides and materials.At the same time,the reaction can also successfully achieve a gram scale,which has potential application value for large-scale production.Chapter three: Study on the [4+2] cyclization reaction of o-aminotrifluoromethyl acetophenones with propiolatesAn efficient [4+2] cyclization reaction of o-aminotrifluoromethyl acetophenones with propiolates has been achieved in this chapter.A series of 1,4-dihydroquinolines were synthesized,which have potentially biologically active.This method has the characteristics of mild reactions,short reaction time,easy operation and it provides a new method for the synthesis of 1,4-dihydroquinolines compounds.This method also expands the synthesis application of o-aminotrifluoromethyl acetophenones as a trifluoromethyl building block.