Synthesis of phthalimide pdf file

Nov 08, 2019 pdf a versatile cucatalyzed crosscoupling reaction to various unsymmetrical disulfanes has been presented, from phthalimidecarried disulfur. Synthesis, spectral characterization and ligation of n2phenylselenoethylphthalimide 33 spectively. An imido derivative of phthalic acid, obtained as a white crystalline substance, c6h4. The neglected tropical disease, schistosomiasis, is caused by trematode blood flukes of the schistosoma genus and infects approximately 200 million people worldwide. 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.

We report the improved process of the synthesis of nphthaloylglycyl hydrazide. 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. This alkylation procedure doesnt produce ammonium salts like the s n 2 reaction would. Phthalimide derivatives of paminosalicylic acid as antituberculosis agents section aresearch paper eur. Rapid and clean synthesis of phthalimide derivatives in high. Reaction of phthalimide with koh removes the nh proton giving an imide ion, a good nucleophile. Practical synthesis of phthalimides and benzamides by a. 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.

Pdf phthalimidecarried disulfur transfer to synthesize. Synthesis, spectral characterization and ligation of n2phenylselenoethyl phthalimide 33 spectively. Maity college of pharmacy, ips academy, rajendra nagar, indore 452012 m. Practical synthesis of a phthalimide based cereblon ligand. Pdf synthesis of some nphthalimide amino acids derivatives and. Linked pdf of table of contents full text pdf 931 kb synform. This is the first report where stability of phthaloyl amino acid compound to hydrazine is demonstrated. Synthesis and application of phthalimide disperse dyes. 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. 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 phthalimide derivatives as potential ppar. Three azo dyes had been synthesized using npropyl substituted, dibromosubstituted and dicyanosubstituted phthalimides as diazo components. Title the reaction between urea and phthalic anhydride. Synthetic of phthalimides via the reaction of phthalic.

Synthesis and hypoglycemic activity of some phthalimide derivatives s. The first step involved reaction of phthalic anhydride with aniline producing nphenyl phthalamic acid 1 which was. 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. 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. The methylation of this compound with diazomethane affords a mixture of nmethyl r 2 nnmeno 2. 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. Supporting information electrochemical dehydrogenative. Some synthetic reactions for preparation of phthalimide moity summarized. Synthesis, molecular docking, and antiepileptic activity of. This challenged the established notion that aa reacts nucleophilically at the nterminal under most conditions. This file is made available under the creative commons cc0 1.

Recent advances and future prospects of phthalimide. This file is licensed under the creative commons attributionshare alike 3. Practical synthesis of a phthalimidebased cereblon ligand. 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. The advantage of this method is that over alkylation is avoided see previous page. Gabriel synthesis generally fails with secondary alkyl halides. The synthesis of 1 commenced with the reduction of 3nitrophthalic anhydride 3 to give 3aminophthalic anhydride 4. Oct, 2018 basically, the reaction uses potassium phthalimide.

What is the mechanism of phthalimide synthesis from phthalic. Phthalimide article about phthalimide by the free dictionary. You may do so in any reasonable manner, but not in. Two methods for the preparation of phthalimide, hive. 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. Solventfree synthesis of phthalimide under microwave. If released to soil, phthalamide should have very high mobility. One approach of this sort begins with the imide phthalimide. Phthalimide is the organic compound with the formula c 6 h 4 co 2 nh. Nsubstituted phthalimide can be prepared by heating anhydride with various ncontaining reagents. The absorption maxima of the dyes were observed in the range 360 to 700. Alkylation of phthalimide gabriel synthesis of primary alkyl amines reaction type.

We report on the design, optimized synthesis, and characterization of a thiophenephthalimide based small molecule. Dec 30, 2017 three azo dyes had been synthesized using npropyl substituted, dibromosubstituted and dicyanosubstituted phthalimides as diazo components. The reaction is named after the german chemist siegmund gabriel, who first posited the synthesis with the aid of his partner, james dornbush. The reaction is named after the german chemist siegmund gabriel, who first posited the. Synthesis, spectral characterization and ligation of n2. Nnitraminophthalimide r 2 nnhno 2 r 2 nh is phthalimide was synthesized by nitration of naminophthalimide with nitronium tetrafluoroborate.

Synthesis of an haggregated thiophenephthalimide based. Files available from the acs website may be downloaded for personal use only. Basically, the reaction uses potassium phthalimide. Structure of phthalimide phthalimide is an imido derivative of phthalic acid. With just one partially effective drug available for disease treatment, new drugs are urgently needed. The dyeing behaviour and fastness properties of these dyes had been investigated. Nnitramino phthalimide r 2 nnhno 2 r 2 nh is phthalimide was synthesized by nitration of naminophthalimide with nitronium tetrafluoroborate. Phthalimide is used as a precursor to anthranilic acid, a precursor to azo dyes and saccharin. The reaction may be explored for the reaction schemes where stability of. 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. Synthesis and chemical modification of maleic anhydride copolymers with phthalimide groups, international journal of industrial chemistry, 20, pp.

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. 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. A variety of phthalimide derivatives have been synthesised effectively in. 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. This anion is a good nucleophile, and is alkylated by alkyl halides or sulfonate esters in s n2 reactions. 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. Synthesis is reported in nanjing gongye daxue xuebao,ziran kexueban, 306, 5153. Deprotonation of the imide nh proton by the base, hydroxide. Phthalimide synonyms, phthalimide pronunciation, phthalimide translation, english dictionary definition of phthalimide. Phthalimide definition of phthalimide by the free dictionary.

Herein, a series of 47 phthalimide pht analogues possessing highvalue bioactive scaffolds i. Saponification of esters gabriel synthesis template synthesis. 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. All of the synthesized intermediates and dyes have been characterized by ms, 1hnmr and ir analyses. Pdf synthesis and characterization of some phthalic acid. Nhydroxyethyl phthalimide pei was prepared by refluxing phthalic anhydride with ethanolamine.

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. 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. 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. Nucleophilic substitution then nucleophilic acyl substitution summary. Recent advances and future prospects of phthalimide derivatives. Synthesis and chemical modification of maleic anhydride copolymers with phthalimide groups. An efficient synthesis of 2,3diaminoacid derivatives. Alkyl halides can be converted to the nalkylphthalimide. Pdf a versatile cucatalyzed crosscoupling reaction to various unsymmetrical disulfanes has been presented, from phthalimidecarried disulfur. Synthesis and hypoglycemic activity of some phthalimide. Practical synthesis of a phthalimidebased cereblon ligand to. Therefore, gabriel phthalimide synthesis is preferred for synthesizing primary amines. Title the reaction between urea and phthalic anhydride under.

Experimental data and characterizations of compounds pdf. Synthesis and bioactivity of phthalimide analogs as. Synthesis of heterocycles from anthranilic acid and its. 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. Gabriel phthalimide synthesis mechanism, synthesis of. Several grave errors in the recent literature were revealed. The potassium salt is the reagent used in the gabriel synthesis. 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. Synthesis of phthaloylglycyl hydrazide derivatives. Synthesis and chemical modification of maleic anhydride. The gabriel synthesis is a great way to make primary amines. 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. Synthesis, structure, and properties of nnitraminophthalimide.

Two methods for the preparation of phthalimide rated as. Full text pdf journal of applied pharmaceutical science. Phthalimide, naminophthalimide, antimicrobial activity, microwave and reflux synthesizer. Zeglam, department of medicinal and pharmaceutical chemistry, faculty of pharmacy, university of tripoli, tripoli. Inspired by the synthesis of phthalimides by the mcr of isocyanides and arynes with co2, we continued. The first technique often produces low yields or side products. 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. 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. For these reasons, other methods for liberating the amine from the phthalimide have been developed. Volatilization of phthalamide may not be important from moist or dry soil surfaces. Saponification of esters gabriel synthesis template. Synthesis of phthalimide derivatives as potential ppar. The absorption maxima of the dyes were observed in the range. Microwaveassisted synthesis of 2substituted 2thiazolines and 5,6dihydro4h1,3thiazines.

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. 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. Two methods for the preparation of phthalimide, hive novel. The structure of this compound was established by xray diffraction and confirmed by 1 h, c, and 14 n nmr spectroscopy. Pdf synthesis of phthalimide derivatives as potential. Synthesis in solventfree conditions can be achieved by refluxing a mixture of phthalic. It is used as a precursor to other organic compounds as a masked source of ammonia. 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. A very neet way of preparing primary amines is by using gabriel synthesis. It is a sublimable white solid that is slightly soluble in water but more so upon addition of base. Phthalimide is sufficiently acidic to form a potassium salt by treatment with concentrated potassium hydroxide solution. Synthesis and characterization of phthalimides 2tertbutylisoindoline1,3dione 3a2 following the general procedure, 2trimethylsilylphenyl trifluoromethane sulfonate 1a 0.

Synthesis, molecular docking, and antiepileptic activity. The reaction is considered to occur through a zwitterionic intermediate derived from the reaction of the. The choice of reaction media was important for selective synthesis of the desired 2,3diaminocarboxylic acid derivatives. Synthesis, structure, and properties of nnitramino. This proton is more acidic than a simple amine due to the resonance stabilisation by the two adjacent co groups. In organic chemistry, imide is a functional group consisting of two carbonyl groups bound to nitrogen. An efficient synthesis of 2,3diaminoacid derivatives using. Potassium phthalimide is treated with base, then a primary alkyl halide, and then either hydrazine, acid, or base. 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. Gabriel phthalimide synthesis mechanism, synthesis of primary. 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. They are hydrophobic and neutral, and can therefore cross biological membranes in vivo. Pdf in this research six of nphthalimides of amino acids iiiaf have been synthesized, as a first step, through cyclocondensation of.