A lewis acid catalyzed and solvent free procedure for the preparation of. The yields of modified copolymers are presented in table 3. Synthesis and antimicrobial activity of phthalimide. Phthalimides production and use in the production of phthalocyanine dyes1, in the synthesis of primary amines and amino acids in the form of its sodium or potassium salt1, as synthetic indigo via anthranilic acid2, as a fungicide2, in organic synthesis2 and as a laboratory reagent2 may result in its release to the environment. Paecilocin a, a phthalide derivative isolated from the jellyfishderived fungus paecilomyces variotii, activates ppar. The gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. This video is highly rated by class 12 students and has been viewed 2124 times.
Two methods for the preparation of phthalimide, hive novel. To synthesize the phthalimide derivatives, initially the reaction was optimized with various catalysts, and l proline was found to be the best catalyst as it provided excellent yield. N 2bromoethylphthalimide c10h8brno2 cid 125 structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safetyhazardstoxicity information, supplier lists, and more. Exhibiting the properties of a weak acid, phthalimide interacts with alkaline solutions, for example, to form metallic derivatives, such as c 8 h 4 o 2 nk, which are used for the synthesis of primary amines.
All of the synthesized intermediates and dyes have been characterized by ms, 1hnmr and ir analyses. Phthalimide is the organic compound with the formula c 6 h 4 co 2 nh. Herein we describe the efficient synthesis of nethyl phthalimide esters 4an. Inspired by the synthesis of phthalimides by the mcr of isocyanides and arynes with co2, we. The preliminary results showed that compared to thalidomide 4a and 4b exhibited enhanced activities against ecv304 and hepg2 cells, whereas 6c was more potent. Chemical extraction of phthalimides by gabriel synthesis using. Phthalimide can be prepared by heating phthalic anhydride with alcoholic ammonia giving 9597% yield.
Heat the flask on an oil bathsand bathheating mantle at 5c till the contents melts, froth up and become solid. After alkylation, the phthalimid is not nucleophile and does not react anymore. The xray analysis revealed the importance of substituents on the crystal stability and molecular packing. Gabriel synthesis is a process of producing amines from alkyl halides. Palladiumcatalyzed aminoallylation of activated olefins with. Lprolinecatalyzed synthesis of phthalimide derivatives and. Alkyl phthalimides are useful precursors to amines in chemical synthesis, especially in peptide synthesis where they are used to block both hydrogens and avoid racemization of the substrates. Phthalimide is converted to potassium salt by treating it with potassium hydroxide koh solution. Ambient carrier mobility of thinfilm transistors prepared from these polymers is as high as 0.
Two methods for the preparation of phthalimide, hive. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided that echa is. Bearing in mind our program in the synthesis of biologically active heterocyclic compounds 2732 and the molecular pharmacophores iv outlined in figure 1 and their structural requirements 3336, some phthalimide derivatives were designed after exploring molecular hybridization approaches with pyrazole, imidazo1,2bpyrazole. The amidomalonate synthesis is a simple variation of the malonic ester synthesis section 22. Rapid and clean synthesis of phthalimide derivatives in high. Further, the molecular structure of majority of compounds were analysed by single crystal xray diffraction studies. What is the mechanism of phthalimide synthesis from phthalic. The gabriel reaction has been generalized to include the alkylation of sulfonamides and imides, followed by deprotection. This alkylation procedure doesnt produce ammonium salts like the s n 2 reaction would. Thinfilm optical and wideangle xray diffraction measurements indicate extended electronic conjugation and close intermolecular. Potassium phthalimide is a nh 2synthon which allows the preparation of primary amines by reaction with alkyl halides. Synthesis, spectral characterization and ligation of n2phenylselenoethylphthalimide 33 spectively. All the synthesized compounds were tested for in vitro.
Request pdf synthesis, structure, and properties of n nitraminophthalimide nnitraminophthalimide r2nnhno2 r2nh is phthalimide was synthesized by nitration of naminophthalimide with. Phthalimide article about phthalimide by the free dictionary. Substituted phthalimides from phthalic acids in one step. Oyo mitsunobu, in comprehensive organic synthesis, 1991.
Synthesis and application of nbutyl substituted phthalimide. Synthesis of anthranilic acid from phthalic anhydride. Synthesis of phthalimide derivatives as potential ppar. Two methods for the preparation of phthalimide rated as. Alternatively, it may be prepared by treating the anhydride with ammonium carbonate or urea. An imido derivative of phthalic acid, obtained as a white crystalline substance, c6h4. Phthalimide is used as a precursor to anthranilic acid, a precursor to azo dyes and saccharin. Synthesis, structure, and properties of nnitramino. Zeglam, department of medicinal and pharmaceutical chemistry, faculty of pharmacy, university of tripoli, tripoli. Covid19 is an emerging, rapidly evolving situation. Typically, nphthalimide derivatives are synthesized using the condensation of amine with phthalic. The most important synthesis of phthalimides is the dehydrative condensation of phthalic anhydride at high temperatures with primary amines, when the amine is available.
Synthesis, structural and antioxidant studies of some novel n. To synthesize the phthalimide derivatives, initially the reaction was optimized with various catalysts, and lproline was found to be the best catalyst as it provided excellent yield. Title the reaction between urea and phthalic anhydride. Synthesis in solventfree conditions can be achieved by refluxing a mixture of phthalic anhydride with the amine or by using a catalyst such as dabco at room. The synthesis and characterization of two new thiophene copolymers with backbone phthalimide units is reported. Dekamin, mohammad g fast and efficient green procedure for the synthesis of benzo5,6chromene derivatives and their sulfur analogues in water by organocatalyst potassium phthalimidenoxyl. The phthalimide carbonyls increase the acidity of the nitrogen thus allowing formation of its conjugate base. What is the mechanism of phthalimide synthesis from. The reaction begins with the deprotonation of the phthalimide which then attacks the alkyl halide in an s n 2 fashion to give an nalkylphthalimide intermediate. A study was planned to synthesize the phthalimide derivatives as phthalimides have versatile biological activities. Finally, the obtained white polymers containing phthalimide substituents in the figure 4 man copolymerization a, sodium phthalimide salt synthesis b, reaction of man copolymer with phthalimide salt c.
Asian journal of pharmaceutical analysis and medicinal chemistry. Download the pdf question papers free for off line practice and view the solutions online. They are hydrophobic and neutral, and can therefore cross biological membranes in vivo. Additionally, by uploading or otherwise transmitting material to any area of the web site you are granting the company. The scope of this transitionmetalfree synthesis of aromatic amides was found to be general. Recent advances and future prospects of phthalimide derivatives.
A very neet way of preparing primary amines is by using gabriel synthesis. Synthesis and chemical modification of maleic anhydride. B97xd6311gd,p calculation found that pistacking interactions of phthalimidebenzene and phthalimidephthalimide dimers increased the. A convenient, efficient, and selective nalkylation of nacidic heterocyclic compounds with alkyl halides is accomplished in ionic liquids in the presence of potassium hydroxide as a base. The threecomponent aminoallylation reaction of the activated olefins 2 with the phthalimide 1a and allyl chloride proceeded very smoothly in the presence of pd2dba3chcl3 5 mol %p4fc6h43 40 mol % and cs2co3 3 equiv against 2 in dichloromethane at room temperature to give the corresponding aminoallylated products, npent4enylphthalimides 3, in 58.
A base abstracts a proton from the alpha carbon, which is then alkylated with an alkyl. Traditionally, the reaction uses potassium phthalimide. Pdf in this research six of nphthalimides of amino acids iiiaf have been synthesized, as a first step. The paper presents the synthesis and characterization of two 4substituted phthalimide 2hydroxyschiff bases containing salicylic 4 and 2hydroxy1naphthyl 5 moieties. Hydrolysis of the phthalimide ring was found to be largely influenced by steric effects rather than inductive effects. Design, synthesis and evaluation of novel phthalimide. When the amine is not readily accessible, the direct n alkylation of phthalimides with alcohols under mitsunobu conditions. Novel phthalimide derivatives 4a, 4b and 6a6e were designed as hybrids of thalidomide and noasa, and their chemical synthesis and in vitro biological activities were presented. In organic chemistry, imide is a functional group consisting of two carbonyl groups bound to nitrogen. Based on a sar structureactivity relationships study and in silico analysis of paecilocin amimetic derivatives, additional nsubstituted phthalimide derivatives were synthesized and evaluated for. Three azo dyes had been synthesized using npropyl substituted, dibromosubstituted and dicyanosubstituted phthalimides as diazo components. It can also be produced by ammoxidation of o xylene.
Other syntheses of phthalimideprotected amino groups. Recent advances and future prospects of phthalimide. Phthalimide is sufficiently acidic to form a potassium salt by treatment with concentrated potassium hydroxide solution. A series of nethyl phthalimide esters 4an were synthesized and characterized by spectroscopic studies. May 01, 2020 gabriel phthalimide synthesis full mechanism class 12 video edurev is made by best teachers of class 12. Phthalimide synonyms, phthalimide pronunciation, phthalimide translation, english dictionary definition of phthalimide.
The neglected tropical disease, schistosomiasis, is caused by trematode blood flukes of the schistosoma genus and infects approximately 200 million people worldwide. Phthalimidebased polymers for high performance organic thin. The reaction is named after the german chemist siegmund gabriel. The synthesized compounds were confirmed from their spectral data. The gabriel synthesis is a great way to make primary amines. Solventfree synthesis of phthalimide under microwave. Pharmaceuticals free fulltext synthesis and bioactivity. May 11, 2009 the synthesis and characterization of two new thiophene copolymers with backbone phthalimide units is reported. Synthesis is reported in nanjing gongye daxue xuebao,ziran kexueban, 306, 5153.
Synthesis and bioactivity of novel phthalimide derivatives. Alkyl halides can be converted to the nalkylphthalimide. Phthalimide definition of phthalimide by the free dictionary. The absorption maxima of the dyes were observed in the range. Synthesis, structural and antioxidant studies of some. The preliminary results showed that compared to thalidomide 4a and 4b exhibited enhanced activities against ecv304 and hepg2 cells, whereas 6c was more potent against hepg2 cells. A series of novel phthalimide derivatives sv 18 have been synthesized and evaluated for antimicrobial activity. Marine drugs free fulltext synthesis of phthalimide. Phthalimidebased polymers for high performance organic. Palladiumcatalyzed aminoallylation of activated olefins. In this process, phthalimide is reacted with alcoholic koh to get potassium phthalimide which reacts with an alkyl halide to form nalkyl phthalimide which on basis hydrolysis gives primary amine and phthalic acid. Phthalimide, naminophthalimide, antimicrobial activity, microwave and reflux synthesizer.
Synthesis, structure, and properties of nnitraminophthalimide. Dec 30, 2017 three azo dyes had been synthesized using npropyl substituted, dibromosubstituted and dicyanosubstituted phthalimides as diazo components. General procedures for synthesis of phthalimide derivatives phethalic anhydride 1 0. Practical synthesis of phthalimides and benzamides by a. Gabriel phthalimide synthesis full mechanism class 12. Herein, a series of 47 phthalimide pht analogues possessing highvalue bioactive scaffolds i. It is used as a precursor to other organic compounds as a masked source of ammonia. Bromo substituted dyes have the lowest rates of hydrolysis. Gabriel synthesis the gabriel synthesis is an organic reaction used to convert an alkyl halide to a primary amine using phthalimide with base and followed by hydrazine. Pdf synthesis of some nphthalimide amino acids derivatives and. Request permission export citation add to favorites track citation. Some synthetic reactions for preparation of phthalimide moity summarized in. Most importantly, the phthalimide carbonyls protect the nitrogen from over alkylation thus preventing the formation of quaternary ammonium salts. The most important synthesis of phthalimides is the dehydrative condensation of.
It is a sublimable white solid that is slightly soluble in water but more so upon addition of base. Ligands by so hyeon eom 1, sen liu 1, mingzhi su 1, tae hwan noh 1, jongki hong 2, nam deuk kim 1, hae young chung 1, min hye yang 1, and jee h. General procedure for the synthesis of pyrazolo5,1c1,2,4triazine derivatives 16 and 17. Gabriel phthalimide synthesis full mechanism class 12 video.
Mix phthalic anhyde 10 g and urea 2 g in a 250 ml rbf. Product is cleaved by reaction with base or hydrazine, which leads to a stable cyclic product. Furthermore, to the best of our knowledge, this is the first report about the transamidation of an aromatic thioamide with amines. The potassium salt is the reagent used in the gabriel synthesis. Therapeutic potential of phthalimide derivatives american journal. The absorption maxima of the dyes were observed in the range 360 to 700. The conformations of the compounds 4an excluding 4d, 4h and 4m were confirmed by single crystal xray diffraction analysis. The phthalimide moiety serves as a protected form of ammonia. The reaction begins with the deprotonation of the phthalimide which then attacks the alkyl halide in an s. Aug 23, 2017 may 01, 2020 gabriel phthalimide synthesis full mechanism class 12 video edurev is made by best teachers of class 12. Lprolinecatalyzed synthesis of phthalimide derivatives. Because the nalkylated phthalimide formed in this reaction is really a double amide, it can be converted into the free amine by amide hydrolysis in either strong acid or base. Peroxisome proliferatoractivated receptor gamma in rat liver ac2f cells.
Potassium phthalimide is treated with base, then a primary alkyl halide, and then either hydrazine, acid, or base. In this manner, phthalimide, indole, benzimidazole, and succinimide can be successfully alkylated. Structure of phthalimide phthalimide is an imido derivative of phthalic acid. A series of phthalimide derivatives was synthesized by facile onetop reaction of phthalic acid. Phthalimide s production and use in the production of phthalocyanine dyes, in the synthesis of primary amines and amino acids in the form of its sodium or potassium salt, as synthetic indigo via anthranilic acid, as a fungicide, in organic synthesis, and as a laboratory reagent may result in its release to the environment through various waste. With just one partially effective drug available for disease treatment, new drugs are urgently needed. Compared with stype dyeing disperse dyes, phthalimide dyes have lower dyeing rates and lower levelness of dye migration. Synthesis, spectral characterization and ligation of n2. An efficient and simple method for the transamidation of carboxamides, phthalimide, ureas and thioamide with amines catalyzed by commercially available benzoic acid under metal. Synthesis and application of phthalimide disperse dyes.
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