سنتز و شناسايي a-آمينونيتريل ها، كومارين ها و 1- آميدوآلكيل-2- نفتول ها با استفاده از مايع يوني اسيدي N- متيل پيروليدونيوم هيدروژن سولفات در شرايط بدون حلال

چكيده انگليسي :

Synthesis and characterization of aminonitrils coumarin 1 amidoalkyl 2 naphthols using acidic ionic liquids N methyl 2 pyrrolidonum hydrogen sulfate under solvent free conditions Maryam Bahrami Miss bahrami@yahoo com Oct 5 2010 Department of Chemistry Isfahan University of Technology 84156 83111 Isfahan IranProf A R Hajipour Email haji@cc iut ac irAbstractMulti component reactions MCRs are very important reactions and they can produce the desire productsin one pot without isolating the intermediates and decreasing the reaction times and using energy therefore these reactions have attracted more interest in modern organic syntheses and researchers have made greatefforts for developing new MCRs In continuation of our effort to develop new and green method inorganic chemistry avoiding using organic solvents during the reactions in organic synthesis Here we wishto report a an efficient one pot reaction under clean and economical conditions green chemistry withstraightforward work up using inexpensive Br nsted acidic ionic liquids in short reaction time with highyield Ionic liquids ILs as green solvents and catalysts have been applied frequently in modern organicreactions due to their specific properties such as high thermal stability undetectable vapor pressure non inflammability and significant advantages in terms of environmental and economic impacts Br nstedacidic ionic liquids were designed to replace traditional mineral acidic in chemical procedures In thisinvestigation N methyl 2 pyrrolidonum hydrogen sulfate H NMP HSO4 was synthesis and its applicationfor synthesize of some organic compounds such as aminonitrils coumarins 1 amidoalkyl 2 naphthols aminonitriles as important intermediates for predation of amino acids and various nitrogen containingheterocycles were investigated The Strecker reaction is one of the general method for synthesize of aminonitrils we did apply this useful acidic ionic liquid for synthesis of aminonitrils from couplingvarious aldehydes and ketones with aniline and trimethylsilyl cyanide under one pot Strecker reaction facile and solvent free conditions The coumarins are versatile heterocyclic organic compounds which alsoare known as benzo 2 pyrone derivatives having various biological activities such as antimicrobial anticancer anti HIV In addition these compounds do have vast application in perfumes agrochemicals cosmetics pharmaceuticals insecticides optical brightening agents dispersed fluorescent and tunable dyelasers industry Also they have widely used as additives in food We employed this catalyst in thePechmann reaction as a well known simple method from the reaction of phenols and ketoesters at 120 oCunder solvent free conditions in good to excellent yields with short reaction times Amidoalkyl 2 naphtolsas useful compounds bearing 1 3 arrangement of amino and oxygenated functional groups are frequentlyfound in biologically important natural products and also are potent biological activities such as nucleosideantibiotics and HIV protease inhibitors Interestingly the 1 amidomethyl 2 naphthols can be converted toimportant biologically active 1 aminomethyl 2 naphthol derivatives by an amide hydrolysis reaction Wealso prepared these important compounds by mixing various aldehydes with acetamide benzamide or ureain the presence of catalytic amount of H NMP HSO4 at 120 oC using an oil bath Kewords Ionic liquid solid state reaction N methyl 2 pyrrolidonum hydrogen aminonitriles coumarin 1 amidoalkyl 2 naphthols

بهرامي، مريم

سنتز و شناسايي a-آمينونيتريل ها، كومارين ها و 1- آميدوآلكيل-2- نفتول ها با استفاده از مايع يوني اسيدي N- متيل پيروليدونيوم هيدروژن سولفات در شرايط بدون حلال

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