Synthesis, spectral characterization and ligation of n2. Pdf a versatile cucatalyzed crosscoupling reaction to various unsymmetrical disulfanes has been presented, from phthalimidecarried disulfur. All of the synthesized intermediates and dyes have been characterized by ms, 1hnmr and ir analyses. This anion is a good nucleophile, and is alkylated by alkyl halides or sulfonate esters in s n2 reactions. Us2919282a us351521a us35152153a us2919282a us 2919282 a us2919282 a us 2919282a us 351521 a us351521 a us 351521a us 35152153 a us35152153 a us 35152153a us 2919282 a us2919282 a us 2919282a authority us united states prior art keywords phthalimide mixture phthalide process zinc prior art date 19530427 legal status the legal status is an assumption and is not a. With just one partially effective drug available for disease treatment, new drugs are urgently needed. An efficient synthesis of 2,3diaminoacid derivatives using. Files available from the acs website may be downloaded for personal use only. Nnitraminophthalimide r 2 nnhno 2 r 2 nh is phthalimide was synthesized by nitration of naminophthalimide with nitronium tetrafluoroborate. Synthesis and hypoglycemic activity of some phthalimide derivatives s. Nov 08, 2019 pdf a versatile cucatalyzed crosscoupling reaction to various unsymmetrical disulfanes has been presented, from phthalimidecarried disulfur. This file is made available under the creative commons cc0 1. We report the improved process of the synthesis of nphthaloylglycyl hydrazide.
Herein, a series of 47 phthalimide pht analogues possessing highvalue bioactive scaffolds i. Synthesis of phthaloylglycyl hydrazide derivatives. Nucleophilic substitution then nucleophilic acyl substitution summary. Synthesis is reported in nanjing gongye daxue xuebao,ziran kexueban, 306, 5153. For these reasons, other methods for liberating the amine from the phthalimide have been developed. Pdf synthesis and characterization of some phthalic acid. Phthalimide article about phthalimide by the free dictionary. Saponification of esters gabriel synthesis template synthesis. The dyeing behaviour and fastness properties of these dyes had been investigated. What is the mechanism of phthalimide synthesis from. Pdf phthalimidecarried disulfur transfer to synthesize. Three azo dyes had been synthesized using npropyl substituted, dibromosubstituted and dicyanosubstituted phthalimides as diazo components. Rapid and clean synthesis of phthalimide derivatives in high. The advantage of this method is that over alkylation is avoided see previous page.
Recent advances and future prospects of phthalimide derivatives. A very neet way of preparing primary amines is by using gabriel synthesis. Supporting information electrochemical dehydrogenative imidation of nmethyl substituted benzylamines with phthalimides for the direct synthesis of phthalimideprotected gemdiamines fei lian, caocao sun, kun xu and chengchu zeng beijing key laboratory of environmental and viral oncology, college of life science. Gabriel phthalimide synthesis mechanism, synthesis of. Phthalimide synonyms, phthalimide pronunciation, phthalimide translation, english dictionary definition of phthalimide. An efficient synthesis of 2,3diaminoacid derivatives.
Experimental data and characterizations of compounds pdf. The reaction may be explored for the reaction schemes where stability of. Synthesis and bioactivity of phthalimide analogs as. The potassium salt is the reagent used in the gabriel synthesis. Phthalimide is the organic compound with the formula c 6 h 4 co 2 nh. Inspired by the synthesis of phthalimides by the mcr of isocyanides and arynes with co2, we continued. Supporting information electrochemical dehydrogenative imidation of nmethyl substituted benzylamines with phthalimides for the direct synthesis of phthalimide protected gemdiamines fei lian, caocao sun, kun xu and chengchu zeng beijing key laboratory of environmental and viral oncology, college of life science. Synthesis, structure, and properties of nnitraminophthalimide. Synthesis and chemical modification of maleic anhydride copolymers with phthalimide groups. Recent advances and future prospects of phthalimide. Pdf synthesis of some nphthalimide amino acids derivatives and. Saponification of esters gabriel synthesis template. What is the mechanism of phthalimide synthesis from phthalic.
Transitionmetalfree multicomponent reactions involving arynes, isocyanides, and co 2 as the third component resulted in the formation of n substituted phthalimides in good yields, whereas the use of water as the third component furnished. Diazotization of 4 and conversion to the corresponding alcohol provided crude 3hydroxyphthalic acid, which was converted to pure 3hydroxyphthalic anhydride 5 via sublimation following the method of eliel. Reaction of phthalimide with koh removes the nh proton giving an imide ion, a good nucleophile. It is used as a precursor to other organic compounds as a masked source of ammonia. If the file has been modified from its original state, some details such as the timestamp may not fully reflect those of the original file. The neglected tropical disease, schistosomiasis, is caused by trematode blood flukes of the schistosoma genus and infects approximately 200 million people worldwide. The structure of this compound was established by xray diffraction and confirmed by 1 h, c, and 14 n nmr spectroscopy. The person who associated a work with this deed has dedicated the work to the public domain by waiving all of their rights to the work worldwide under law, including all related and neighboring rights, to the extent allowed by law. Pdf synthesis of phthalimide derivatives as potential ppar. 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. Practical synthesis of phthalimides and benzamides by a. Synthesis of welldefined phthalimide monofunctional hyperbranched polyglycerols and its transformation to various conjugation relevant functionalities gyorgy kasza1, gergely kali2, attila domjan3, lilla petho4, gyorgyi szarka1 and bela ivan1 1polymer chemistry research group, institute of materials and environmental chemistry and. This is the first report where stability of phthaloyl amino acid compound to hydrazine is demonstrated. The synthesis of 1 commenced with the reduction of 3nitrophthalic anhydride 3 to give 3aminophthalic anhydride 4.
Synthesis, molecular docking, and antiepileptic activity. Volatilization of phthalamide may not be important from moist or dry soil surfaces. Synthesis, structure, and properties of nnitramino. Synthesis of phthalimide february 23, 2016 december 23, 2017 organic combine fine powders of 70 g of phthalic anhydride with 23 g of urea, pour the mixture 1 l rbf, heat the mixture strongly. Synthesis and hypoglycemic activity of some phthalimide. Phthalimides 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. Linked pdf of table of contents full text pdf 931 kb synform. If you would like more information about how to print, save, and work with pdfs, highwire press provides a helpful frequently asked questions about pdfs. Synthesis and chemical modification of maleic anhydride copolymers with phthalimide groups, international journal of industrial chemistry, 20, pp. The methylation of this compound with diazomethane affords a mixture of nmethyl r 2 nnmeno 2. We report on the design, optimized synthesis, and characterization of a thiophenephthalimide based small molecule. They are hydrophobic and neutral, and can therefore cross biological membranes in vivo. According to the previous study, the introduction of hydroxyl groups would allow the phthalimide moiety to be more effective as a polar head group and this modification could be further extended using linker and tail groups to generate potential ppar. Nnitramino phthalimide r 2 nnhno 2 r 2 nh is phthalimide was synthesized by nitration of naminophthalimide with nitronium tetrafluoroborate.
Synthesis, spectral characterization and ligation of n2phenylselenoethylphthalimide 33 spectively. Us2919282a us351521a us35152153a us2919282a us 2919282 a us2919282 a us 2919282a us 351521 a us351521 a us 351521a us 35152153 a us35152153 a us 35152153a us 2919282 a us2919282 a us 2919282a authority us united states prior art keywords phthalimide mixture phthalide process zinc prior art date 19530427 legal status the legal status is an assumption and is not a legal conclusion. Nhydroxyethyl phthalimide pei was prepared by refluxing phthalic anhydride with ethanolamine. 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. Synthesis, molecular docking, and antiepileptic activity of. Title the reaction between urea and phthalic anhydride. The reaction is considered to occur through a zwitterionic intermediate derived from the reaction of the. Organic chemistry chapter 19 amines nomenclature basicity synthesis gabriel synthesis template synthesis using phthalimide nh o o n o o r baoh 2 nh 2 nh 2 r nh 2 o o o o 1. Therefore, gabriel phthalimide synthesis is preferred for synthesizing primary amines. Supporting information electrochemical dehydrogenative. Synthesis of an haggregated thiophenephthalimide based. A variety of phthalimide derivatives have been synthesised effectively in.
Two methods for the preparation of phthalimide, hive. 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. Several grave errors in the recent literature were revealed. Synthesis, spectral characterization and ligation of n2phenylselenoethyl phthalimide 33 spectively. Alkyl halides can be converted to the nalkylphthalimide. Structure of phthalimide phthalimide is an imido derivative of phthalic acid. Pdf in this research six of nphthalimides of amino acids iiiaf have been synthesized, as a first step, through cyclocondensation of. In organic chemistry, imide is a functional group consisting of two carbonyl groups bound to nitrogen. Synthesis and characterization of phthalimides 2tertbutylisoindoline1,3dione 3a2 following the general procedure, 2trimethylsilylphenyl trifluoromethane sulfonate 1a 0. If released to soil, phthalamide should have very high mobility. The pdf file you selected should load here if your web browser has a pdf reader plugin installed for example, a recent version of adobe acrobat reader if you would like more information about how to print, save, and work with pdfs, highwire press provides a helpful frequently asked questions about pdfs alternatively, you can download the pdf file directly to your computer, from where it. This alkylation procedure doesnt produce ammonium salts like the s n 2 reaction would.
We show that microwave irradiation is a useful technique to accelerate direct arylation crosscoupling reactions, and that the thiophenephthalimide architecture can lead to facetoface intermolecular. Phthalimide and nsubstituted phthalimides are an important class of compounds because they possess important biological activities including antiinflammatory activity 1, analgesic activity 2 and hypolipidemic activity 3, and also it is used in organic synthesis and other industrial fields such as in drugs synthesis for the. Dec 30, 2017 three azo dyes had been synthesized using npropyl substituted, dibromosubstituted and dicyanosubstituted phthalimides as diazo components. Two methods for the preparation of phthalimide, hive novel. Synthesis of heterocycles from anthranilic acid and its. This file is licensed under the creative commons attributionshare alike 3. Zeglam, department of medicinal and pharmaceutical chemistry, faculty of pharmacy, university of tripoli, tripoli. The absorption maxima of the dyes were observed in the range 360 to 700. Phthalamides production and use as an intermediate in organic synthesis and as a laboratory reagent may result in its release to the environment through various waste streams. This proton is more acidic than a simple amine due to the resonance stabilisation by the two adjacent co groups.
Oct, 2018 basically, the reaction uses potassium phthalimide. The absorption maxima of the dyes were observed in the range. Title the reaction between urea and phthalic anhydride under. Potassium phthalimide is treated with base, then a primary alkyl halide, and then either hydrazine, acid, or base. Phthalimide, naminophthalimide, antimicrobial activity, microwave and reflux synthesizer. 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. The reaction begins with the deprotonation of the phthalimide which then attacks the alkyl halide in an s. Alkylation of phthalimide gabriel synthesis of primary alkyl amines reaction type. Practical synthesis of a phthalimidebased cereblon ligand. Practical synthesis of a phthalimide based cereblon ligand. Solventfree synthesis of phthalimide under microwave. Phthalimide derivatives of paminosalicylic acid as antituberculosis agents section aresearch paper eur. Two methods for the preparation of phthalimide rated as.
One approach of this sort begins with the imide phthalimide. The first technique often produces low yields or side products. This file contains additional information such as exif metadata which may have been added by the digital camera, scanner, or software program used to create or digitize it. Some synthetic reactions for preparation of phthalimide moity summarized. If you do not see its contents the file may be temporarily unavailable at the journal website or you do not have a pdf plugin installed and enabled in your browser. Full text pdf journal of applied pharmaceutical science. Synthesis in solventfree conditions can be achieved by refluxing a mixture of phthalic. Microwaveassisted synthesis of 2substituted 2thiazolines and 5,6dihydro4h1,3thiazines.
Phthalimide is used as a precursor to anthranilic acid, a precursor to azo dyes and saccharin. Phthalimide is sufficiently acidic to form a potassium salt by treatment with concentrated potassium hydroxide solution. Gabriel synthesis generally fails with secondary alkyl halides. Deprotonation of the imide nh proton by the base, hydroxide. Gabriel phthalimide synthesis mechanism, synthesis of primary.
The pdf file you selected should load here if your web browser has a pdf reader plugin installed for example, a recent version of adobe acrobat reader. Practical synthesis of a phthalimidebased cereblon ligand to. The first step involved reaction of phthalic anhydride with aniline producing nphenyl phthalamic acid 1 which was. Synthesis and application of phthalimide disperse dyes. 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. The reaction is named after the german chemist siegmund gabriel, who first posited the. The gabriel synthesis is a great way to make primary amines. An imido derivative of phthalic acid, obtained as a white crystalline substance, c6h4. You may do so in any reasonable manner, but not in. Pdf synthesis of phthalimide derivatives as potential. Synthetic of phthalimides via the reaction of phthalic. Dekamin, mohammad g fast and efficient green procedure for the synthesis of benzo5,6chromene derivatives and their sulfur analogues in water by organocatalyst potassium phthalimide noxyl.
Phthalimide definition of phthalimide by the free dictionary. Maity college of pharmacy, ips academy, rajendra nagar, indore 452012 m. The choice of reaction media was important for selective synthesis of the desired 2,3diaminocarboxylic acid derivatives. Nsubstituted phthalimide can be prepared by heating anhydride with various ncontaining reagents. This challenged the established notion that aa reacts nucleophilically at the nterminal under most conditions. Synthesis of phthalimide derivatives as potential ppar. Jun 08, 2016 based on a sar structureactivity relationships study and in silico analysis of paecilocin amimetic derivatives, additional nsubstituted phthalimide derivatives were synthesized and evaluated for ppar. Basically, the reaction uses potassium phthalimide.