Phthalimide, naminophthalimide, antimicrobial activity, microwave and reflux synthesizer. The absorption maxima of the dyes were observed in the range. Synthesis of phthalimides crossconjugated with an azulene. The protocol has generated a broad range of phthalimide derivatives in good to excellent yields. Application phthalimide was used in the synthesis of 6amino agarose aa by mitsunobuinspired microwave mediated method packaging 1 kg in poly bottle. The reaction is named after the german chemist siegmund gabriel, who first posited the synthesis. H carbonylation of benzoyl hydrazides with carbon monoxide. Request pdf synthesis and characterization of new soluble polyamides containing phthalimide pendent group a dicarboxylic acid monomer, 5phthalimidoisophthalic acid, containing a phthalimide. Solventfree synthesis of phthalimide under microwave. Phthalimide derivatives of paminosalicylic acid as antituberculosis agents section aresearch paper eur. Potassium phthalimide is treated with base, then a primary alkyl halide, and then either hydrazine, acid, or base. To overcome the above difficulties, imines are used as the amine source to achieve aminocarbonyl celebrating the 90th birthday of professor lu xiyan organic chemistry frontiers hot.
Synthesis and characterization of novel diblock copolymers of 5 ncarbazoyl methylbicyclo2. Phthalimide is used as a precursor to anthranilic acid, a precursor to azo dyes and saccharin. The dyeing behaviour and fastness properties of these dyes had been investigated. Although alkylation of phthalimide can now be performed under mild conditions as described in the preceding section, the final deprotection step still requires somewhat drastic conditions, e. An efficient and simple method enables the nalkylation of aromatic cyclic imides using cesium carbonate as the base in anhydrous n,ndimethylformamide at low temperatures 2070. Download zip file 5kb zip file containing the mol files of the most important compounds in this article. Synthesis and characterization of new soluble polyamides.
Synthesis, spectral characterization and ligation of n2phenylselenoethyl phthalimide 33 spectively. The synthesis of isomerically pure allylic amines, including farnesyl amine, is achieved in excellent yields using a modified gabriel synthesis. Rapid and clean synthesis of phthalimide derivatives in high. Zeglam, department of medicinal and pharmaceutical chemistry, faculty of pharmacy, university of tripoli, tripoli. Three azo dyes had been synthesized using npropyl substituted, dibromosubstituted and dicyanosubstituted phthalimides as diazo components. Cobaltcatalyzed carbonylative synthesis of phthalimides.
Moe key laboratory of bioorganic phosphorous chemistry and chemical biology, department of chemistry, tsinghua university, beijing 84, china email. Synthesis and application of phthalimide disperse dyes. Nucleophilic substitution then nucleophilic acyl substitution summary. Dry ch3cn was purchased from commercial sources and stored under argon over 4 a molecular sieves.
The subsequent procedure is the same as when aqueous ammonia is used. Experimental procedures, characterization of products and. The idea here is to use a bulky nitrogen which can only perform one nucleophilic substitution the nh bond of the imide, being between two electronwithdrawing carbonyl groups, is quite acidic pka 8. 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. Gabriel phthalimide synthesis mechanism, synthesis of. 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. The novel method also proved applicable for the synthesis of heteroaromatic unsymmetric diamides as well. Synthesis and anion binding properties of phthalimide. In organic chemistry, imide is a functional group consisting of two carbonyl groups bound to nitrogen. A base abstracts a proton from the alpha carbon, which is then alkylated with an alkyl. Traditionally, the reaction uses potassium phthalimide. Frequent shaking is necessary, and the sublimed material must be pushed back occasionally into the reaction flask.
Experimental data and characterizations of compounds pdf. Synthesis of phthalimide derivatives as potential ppar. Convenient synthesis of phthalocyanines with disilazanes. 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. Reaction of phthalimide with koh removes the nh proton giving an imide ion, a good nucleophile. Phthalimide is a dicarboximide that is 2,3dihydro1hisoindole substituted by oxo groups at positions 1 and 3. Phthalimide formation of phthalic anhydride with various amines using microwave or. A very neet way of preparing primary amines is by using gabriel synthesis. The following zip file contains the mol files of the most important compounds referred to in this article. Recent advances and future prospects of phthalimide. It can also be produced by ammoxidation of oxylene. Alternatively, it may be prepared by treating the anhydride with ammonium carbonate or urea.
Practical synthesis of a phthalimidebased cereblon ligand. This file is licensed under the creative commons attributionshare alike 3. What is the mechanism of anthranilic acid synthesis from. It still remains a challenge due to the decomposition of catalysts and poor chemoselectivity. So, to convert the nitrogen into a better nucleophile, it is first deprotonated by a hydroxide or. Such an arrangement of carbonyl groups about the nitrogen atom causes the compounds involved to be slightly acidic. Arylthio phthalimides as the electrophilic sulfur source soumya dutta department of chemistry, jadavpur university, jadavpur, kolkata 700032 india. The gabriel synthesis of primary amines chemistry steps. Files available from the acs website may be downloaded for personal use only. Title the reaction between urea and phthalic anhydride. Pdf in this research six of nphthalimides of amino acids iiiaf have been synthesized, as a first step, through cyclocondensation of.
Synthesis and antiinflammatory activity of phthalimide derivatives, designed as new thalidomide analogues. Isatoic anhydride is a very useful intermediate in industry for making things and stuff. Synthesis, spectral characterization and ligation of n2. The reaction proceeded through a mechanistically unique insertion of a cycloruthenated species into a c het multiple bond of isocyanate. Thf was purified by distillation over nabenzophenone and was transferred under argon.
Alkylation of the phthalimide anion gabriel synthesis gabriel devised a method for the preparation of primary amines unaccompanied by impurities of secondary or tertiary amines. Some synthetic reactions for preparation of phthalimide moity summarized. Two methods for the preparation of phthalimide rated as. Supporting information electrochemical dehydrogenative. Synthetic of phthalimides via the reaction of phthalic. Synthesis and anion binding properties of phthalimide containing corona6arenes mengdigu, yaolu andmeixiangwang full research paper open access address. Methods of synthesis phthalimide derivatives and biological activity.
Phthalimide is the organic compound with the formula c6h4co2nh. Alkylation of phthalimide gabriel synthesis of primary alkyl amines reaction type. Pdf synthesis of some nphthalimide amino acids derivatives and. Various phthalimide derivatives were obtained in moderate to excellent yields up to 98% by using 2picolylamine as an efficient directing group and benzene1,3,5triyl triformate tfben as a convenient co surrogate. Synthesis in solventfree conditions can be achieved by refluxing a mixture of phthalic. This alkylation procedure doesnt produce ammonium salts like the s n 2 reaction would. A cobaltcatalyzed direct carbonylative synthesis of phthalimide motifs from n pyridin2ylmethyl benzamides has been developed.
Synthesis is reported in nanjing gongye daxue xuebao,ziran kexueban, 306, 5153. This challenged the established notion that aa reacts nucleophilically at the nterminal under most conditions. The employment of microwave irradiation presents noteworthy advantages over. You may do so in any reasonable manner, but not in. Structure of phthalimide phthalimide is an imido derivative of phthalic acid. Alkyl phthalimides are useful precursors to amines in chemical synthesis, especially in peptide. The advantage of this method is that over alkylation is avoided see previous page. Synthesis of anthranilic acid from phthalic anhydride. Synthesis and anion binding properties of phthalimide containing corona6arenes mengdi gu, yao lu and meixiang wang. Nuclophilic attack of amino group of urea towards one of the carbonyl group of phthalic anhydride forms intermediate substituted pthalamide. Therefore, gabriel phthalimide synthesis is preferred for synthesizing primary amines. This is called the gabriel synthesis and it relies on phthalimide as the nucleophile. Synthesis of nsubstituted phthalimidoalkyl 1h1,2,3triazoles.
This file is made available under the creative commons cc0 1. The obtained propiolate was further transformed to various 3,4. All of the synthesized intermediates and dyes have been characterized by ms, 1hnmr and ir analyses. Basically, the reaction uses potassium phthalimide. The gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. Pdcatalyzed ch bond aminocarbonylation represents one of the most significant approaches to the synthesis of amides. They are hydrophobic and neutral, and can therefore cross biological membranes in vivo. The reaction is named after the german chemist siegmund gabriel. Hmds also realized the first synthesis of metalfree phthalocyanines from phthalimides and phthalic anhydrides. Why cannot aromatic primary amines be prepared by gabriel phthalimide. The reaction begins with the deprotonation of the phthalimide which then attacks the alkyl halide in an s n 2 fashion to give an. 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. Phthalimide article about phthalimide by the free dictionary.
Amides get a molecular rearrangement hoffmann rearrangement with solutions of sodium or potassium hypobromide to give primary amines. The structure, optical and electrochemical pr synthetic methodology in obc. Selective formation of phthalimides from amines, aldehydes. Phthalimide has a nitrogen atom flanked by two carbonyl groups. What links here related changes upload file special pages permanent link page. 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. Pdf synthesis and characterization of some phthalic acid. Nsubstituted phthalimide can be prepared by heating anhydride with various ncontaining reagents.
Inspired by the synthesis of phthalimides by the mcr of isocyanides and arynes with co2, we continued. Phthalimide can be prepared by heating phthalic anhydride with aqueous ammonia giving 9597% yield. For the synthesis of phthalimides, all reactions were carried out under an atmosphere of co2 balloon. Commercially, anthranilic acid is prepared using phthalimide or phthalic anyhdride. What is the mechanism of phthalimide synthesis from. This is known as the hofmann degradation or hofmann amine synthesis. View the article pdf and any associated supplements and figures for a period of 48 hours. Synthesis and anion binding properties of phthalimide containing corona6arenes. A variety of phthalimide derivatives have been synthesised effectively in. Synthesis of heterocycles from anthranilic acid and its. Two methods for the preparation of phthalimide, hive. Practical synthesis of phthalimides and benzamides by a. 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. The gabriel synthesis is a great way to make primary amines.
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