The Synthesis And Application Of α-oxo Ketene Dithioacetals

As versatile intermediates, α-oxo ketene dithioacetals have been applied extensively insynthesis, especially in recent decades.They were studied a lot as1,3-electrophiles to formaroy and heterocyclic compounds, but researches on the α-carbon atom of these intermediatesare limited.Someone had done some researches in this field, but the usage is limited for theflexibility about the functional groups on the α-carbon atom.In this paper, the reactions on the α-carbon atom of ketene dithioacetals were exploited,the α-position of ketene dithioacetals were functionlized by diazonium etc;And thecondensation reaction of the compounds obtained on the above were done and studied thereduction of sulfur aldehyde chemical reaction of2-(1,3-dialkyl thio)-methylene-3-carbonylsuccinic amide as the generation of thiol reagents.1、The reaction of α-oxo ketene/carboxyl ketene dithioacetals and aryl diazonium saltwere studied, five compounds of1-(1,3-dithiolane ring/dithiane)-2-methylene-1-arylazoacetones were successfully obtained.2、On the basis of the study complied,1-phenylazo-1-(1,3-dithiolane ring-2-ylidene)-4-phenylbutyrate ketene was obtained and studied, and a condensation reaction product was got.3、Under the conditions of2-(1,3-dialkylthio)-3-oxo butyric amide on behalf of thiolreagents,ethanol as solvent,and benzoyl chloride as a catalyst, Nine synthesis of thio acetalcompounds were got.The products are characterized on IR and1HNMR.On the first time,we Completedreaction of α-oxo ketene/carboxyl ketene dithioacetals with aryl diazonium salt in a simpleoperation.We also solved the addresses about the environment and security issues of relativelyLow molecular weight thiols in the reduction of sulfur aldehyde/ketone chemistry reaction.And we have a preliminary discussion of the above reaction mechanism.