| Halogen is a common easily-leaving group,so halogen-containing compounds are an important organic synthetic intermediates in organic synthesis.Introducing of halogen atoms into organic compounds to prepare halogen-containing compounds is a very important research field in the chemical community.Trichloroisocyanuric acid is an efficient,safe,cheap and readily available solid chlorinating agent.Meanwhile,it is still a high-efficiency,low-toxic bactericides bleaches and wool anti-shrinking agents,also known as "Strong chlorine" in the industry,referred to as "TCCA".TCCA is also often used as a free radical initiator in the organic synthesis.This article focuses on the introduction of chlorine atoms into a-cyano ketones and 1,3-dicarbonyl compounds using trichloroisocyanuric acid as the chlorine source.In this dissertation,a series of investigations on the synthesis of indole oxide via a free radical cyclization promoted by trichloroisocyanuric acid were presented.At the same time,this dissertation also studied on the segment synthesis of Rubesanolide A.This thesis is divided into four parts.Chapter one:Research progress of chlorination reaction involved in trichloroisocyanuric acidThis chapter focuses on a brief review of the chlorination of trichloroisocyanuric acid.The various chlorination reactions in which trichloroisocyanuric acid is involved are described.The substrates contain:alkanes,alkenes,alkynes,alcohol,aldehydes,ketones,1,3-dicarbonyl compounds.Chapter two:Trichloroisocyanuric acid as chloride source for chlorination of a-cyano ketones and 1,3-dicarbonyl compoundsIn this chapter,TCCA was used as a chlorine source to access the chlorination of a-cyano ketones and 1,3-dicarbonyl compounds.The chlornation of a-cyanoketone and 1,3-dicarbonyl compounds were successfully reported with good yield via this method.Chapter three:TCCA promotes chlorination/carbocyclic tandem reaction of acrylamide to synthesize cerium oxide compoundsIn this chapter,TCCA was used as a free radical initiator and a chlorine source to induce the cascade chlorination/carbocyclic reaction of N-methyl-N-phenylmethacrylamides.The indole oxide compounds were constructed and the target product yield was up to 72%.Chapter four:The segment synthesis of Rubesanolide A racemateIn this chapter,the synthesis of ABC tricyclic system in rubesanolide A was studied from inexpensive 3-methoxybenzaldehyde as the starting material.This part mainly includes the bromination reaction of benzene,nucleophilic addition reaction of aldehyde,reduction double bond with NaBH4 and decarboxylation and other reactions.The desired product to prepared the segment was obtained in 52%over all yield. |
