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The Organic Reactions Catalyzed By Cyanuric Chloride

Posted on:2010-03-04Degree:MasterType:Thesis
Country:ChinaCandidate:P ZhangFull Text:PDF
GTID:2121360275955888Subject:Organic Chemistry
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Organic catalysts are used widly in organic reactions.Many organic reactions,which originally can't be carried out or are difficult to operate,have be successfull performed in mild conditions in the presence of organic catalysts.The fields of organic catalysts are expanding and will boost the development new synthetic methods under milder conditions,atom economies with high yields and selectivities in 21 century.With increasing environmental concerns and the need for efficient and green organic catalysts for various useful organic transformations,In recent years,2,4,6-trichloro- 1,3,5-triazine(TCT,cyanuric chloride) has been used in organic synthesis.Because it is stable,nonvolatile,inexpensive,commercially available,and easy-to-handle reagent.It is therefore widely used in the field of organic synthesis.In this paper,the work of our predecessors is on the basis of organic catalyst-cyanuric chloride in organic synthesis of new applications.First,cyanuric chloride(TCT) is an organic catalyst in organic synthesis.The reaction of cyanuric chloride has three main groups involving the protection of the formation and decomposition,addition reaction,the cycloaddition reaction,cyclization,rearrangement, oxidation and reduction reactionsThe use of environment-friendly medium in lieu of the general reaction of the organic solvent fits for the requirements of green chemistry.But even so,still in the reaction will inevitably bring,such as recycling and treatment and other questions.Therefore,the best strategy is to not use solvents.Solvent-free reactions conditions is more fit for the requirements of green chemistry.It can significantly reduce the solvent resulting from recycling,treatment and pollution problem.Solvent-free reactions could also become a catalyst efficiency problem to solve one of the ways we herein report a new,convenient,and one-reaction step synthesis of benzopyran derivatives by treatment of substituted salicyaldehydes and substituted 1,3-hexane- dione in the presence of catalytic amount of cyanuric chloride(TCT)under solvent-free conditions The reaction proceeds smoothly in shortly reaction time under solvent-free conditions.This method is suitable for various substrates,operational and experimental simplicity.Most of compounds were characterized by and 1H NMR,13C NMR and IR.Compounds bearing 1,3-arrangement of amino and oxygenated functional groups are frequently found in biologically important natural products.Furthermore,amidoalkyl naphthols can be converted to useful synthetic building blocks.The preparation of amidoalkyl naphthols can be carried out by multicomponent condensation of aldehydes,2-naphthol and amide or urea in the presence of Lewis or Br?sted acid.How ever,some of the reported methods suffer from disadvantages such as long reaction time,the use of expensive reagents, low yields of products,corrosive reagents,strongly acidic conditions,and the use of an additional microwave oven or ultrasonic irradiation.Therefore,to avoid these limitations,we developed a new application for cyanuric chloride(TCT).By using this catalyst,a series of amidoalkyl naphthols were obtained in high yields under solvent-free conditions.The synthesis of xanthene derivatives have been of considerable interest to pharmaceutically chemist and organic chemist because of their widly range of biological and pharmaceutical properties such as anti-dysplasia,anti-bacterial,anti-allergy,anti-cancer activities,and used to treatment of allergic trachitis and diabetes.In addition,these compounds are structural units of many natural products and important heterocyclic compounds intermediate.Therefore,the synthesis of xanthenes derivatives are present research hot spot.Traditionally method of synthesis of xanthenes derivatives are reaction of aldehydes with carbonyl compounds which containing active methylene compounds under acidic conditions or alkali conditions.The key for these reactions are to search an effective catalyst.The efficacy of various catalysts are tested for this conversion and cyanuric chloride(TCT) was found to be superior in terms of yields and reaction rates.The method is applicable to a wide range of aldehydes.The reaction proceeds smoothly in short reaction time under solvent-free conditions.In conclusion,cyanuric chloride as promoter and catalyst demonstrated the importance and advantages in many important organic transformations.Despite of the significant progress in the applications of cyanuric chloride(TCT) as catalysts in diverse organic synthesis have been achieved,the search for some novel synthetic process involving cyanuric chloride(TCT) will continue to be an interesting and challenging research topic.On the basis of that pioneering works,the new applications of cyanuric chloride(TCT) as organic catalysts in organic synthesis have been expanded.The research of new applications of cyanuric chloride(TCT) will renew and expand for classical acid and base theory in organic chemistry, these will provide a platform and open up a new path for the search for new reagents,the establishment of new methods and new theories.It will promote the development of organic synthesis chemistry.
Keywords/Search Tags:cyanuric chloride, organic catalysts, benzopyran derivatives, amidoalkyl naphthols, xanthenes
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