Syhthesis following methods were reported for the synthesis of oxoquinazolines. The most common synthetic method of the 3h quinazolin4one ring is based on the niementowski reaction, which involves the fusion of anthranilic acid. Synthesis of new 1,2,3triazol4ylquinazoline nucleoside and. Chapter synthesis and biological evaluation of some. Other readers will always be interested in your opinion of the books youve read. Synthesis of quinazolinones and quinazolines request pdf. A new and facile preparation of quinazoline 2,41h,3hdiones was first reported which was the condensation of aromatic oaminonitriles with dmf or n,ndiethylformamide in the presence of zncl2 0. Files are available under licenses specified on their description page. Niementowskis synthesis compound 3 or 4substituted anthranilic acid when reacted with formamide at 125c gave 3,4dihydro4oxoquinazoline see scheme 8. This method offers the advantages of proceeding in neutral conditions, giving high to excellent isolated yields 8392% for niementowski synthesis with easy workup procedure. When the effervescence ceased, the precipitate obtained was filtered and washed with water. In conclusion, we reported the design and synthesis of four 2,4disubstituted quinazoline series containing various amide moieties and tested their antiinfluenza awsn33 h1n1 virus activities. The essence of the synthesis is given in equation 8.
Reduction of this with zinc and dilute acetic acid gave quinozoline in. Synthesis of heterocycles from anthranilic acid and its derivatives. Jun 03, 20 owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. Synthesis and applications of quinazolinebased fluorescent. Recently, many efforts have been focused by chemists on the modification of quinazoline ring for development of pharmaceutical and clinical compounds. A highly employed method for 43hquinazolinone synthesis is based on acylation of anthranilic acid with acyl chloride. Synthesis of some novel quinazoline derivatives having anticancer activity. Owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. Microwave assisted synthesis and molecular docking. Niementowski quinazoline synthesis, cheminform on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. In this paper, we report the synthesis of nsubstituted3nitrophthalimide derivatives iiiii, the reactions of phthalimide iii with amines, hydrazines, and amino acid derivatives to synthesise a small library of 3substituted5. In 1903, siegmund gabriel reported the synthesis of the parent quinazoline from onitrobenzylamine, which was reduced with hydrogen iodide and red phosphorus to 2aminobenzylamine. Molecular iodine catalyses a benzylic sp 3 ch bond amination of 2aminobenzaldehydes and 2aminobenzophenones with benzylamines to provide quinazolines in very good yields. A simple and efficient approach for the synthesis of 2aminoquinazoline derivatives in moderate to good yields.
A simple and efficient approach for the synthesis of 2. Compounds 1 and 2 demonstrated a remarkable antiproliferative effect, with an ic 50 value of 6. Chemical characteristics, synthetic methods, and biological. A new series of 8substituted43h quinazoline derivatives were synthesized, evaluated for their anticonvulsant activity against chemically ptz, picrotoxin and strychnine and electrically mes induced seizures and compared with the reference drugs valproate and methaqualone. Quinazolines and quinazolinones constitute a major class of biologically active molecules both from natural and synthetic sources. The structure and activity relationship in this study indicated that the triketonecontaining quinazoline2,4dione motif has possessed great impact on herbicide activity and may be used for further optimization. Niementowski was een voornaam scheikundige in zijn tijd. Synthesis of quinazoline from ring closure of anthranilic acid or its derivatives. Synthesis of some novel quinazoline derivatives having anti. Pdf synthesis and biological evaluation of some quinazoline. Quinazoline is a compound made up of two fused sixmembered simple aromatic rings, a benzene ring and a pyrimidine ring. The use of oxygen as an oxidant combined with the transitionmetal, additive and solventfree. Research has demonstrated that the niementowski quinazoline synthesis could be employed for the creation of potential egfrinhibiting molecules. The pasty mass obtained was diluted with 50ml of water and treated with aqueous sodium bicarbonate solution.
This reaction employs mild reaction conditions, is metalfree and utilizes readily available starting materials making it a more viable reaction for scale up synthesis and ligand diversity. Stefan niementowski zjovkva, 4 augustus 1866 warschau, juli 1925 was een pools scheikundige. Quinazoline is a mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms. Synthesis and reactivity of some novel quinazoline. The use of oxygen as an oxidant combined with the transitionmetal, additive and solvent. Because of the similarity of these to the reagents in the friedlander quinolone synthesis, a benzaldehyde with an aldehyde or ketone, the niementowski quinoline synthesis mechanism is minimally different from that of the friedlander. Quinazoline in 1905 riedel obtained a patent describing a synthesis of quinazoline from onitrobenzaldehyde through reaction with formamide to the onitrobenzylidenediformamide. A fourcomponent procedure for the preparation of substituted quinazolines from anilines, aromatic aldehydes and ammonium iodide is described. In this paper the onestep synthesis of the novel pyrido2,3.
Acid hydrazide, acetylhydrazine carboxylate and acetylhydrazinecarbodithioate were the most active compounds with. Many of them exhibit potent in vitro antiiav activity and low cytotoxicity cc 50. Introduction 4 microwave irrigation for synthesis quinazolinone modifiation of niementowski reaction were carried out by microwave assisted synthesis,39 an equimolar amount of the reactants were mixed and irradiated under microwaves40 to provide the yield. Synthesis, characterization, and anticancer activity of new.
Oct 17, 2012 3substituted quinazoline2,41h,3hdione and 2,3disubstituted quinazolineone derivatives attract considerable interest due to their pharmacological properties. Synthesis of nheterocycles benzofused nheterocycles synthesis of quinazolines. A family of quinazoline based fluorescent nucleoside analogues is synthesized for photophysical studies and applications in probing nucleic acid structure, dynamics, and recognition. Medicinally it has been used in various areas especially as an antimalarial agent and in cancer treatment. A sustainable synthesis of quinazoline and 2aminoquinoline via acceptorless dehydrogenative annulation is catalyzed by earthabundant welldefined manganese complexes bearing nns ligands. Modifiation of niementowski reaction were carried out by. The niementowski quinazoline synthesis is the chemical reaction of anthranilic acids with amides to form 4oxo3,4dihydroquinazolines 3hquinazolin4ones. Quinazolinone derivatives are an important class of these heterocyclic compounds. Devi and coworkers have reported the synthesis of some new aza isatin derivatives containing 43h quinazolinones. The niementowski quinazoline synthesis is the chemical reaction of anthranilic acids with amides to form 4oxo3, 4dihydroquinazolines. Various methods were reported for the synthesis of oxoquinazolines. The nhexyl substituted isatin quinazoline derivative has been found to be relatively active against screened gram positive, gram negative bacteria and fungi species in comparison to other compounds fig.
Biological activities of quinazolines diverse biological activities were attributed to compounds possessing a quinazoline ring system. Among the new compounds, iiib and viavid displayed a broader spectrum of weed control than mesotrione. Typically, quinazolin43hones are prepared from an anthranilic acid or its derivative, e. The synergy of combined use of dmso and bronsted acid. Synthesis, characterization, and anticancer activity of. Onepot synthesis of quinazolinone and benzamide derivatives. The thermal transformation of an anthranilic acid into 4. We initiated this study with the goal of expanding the efficacy and efficiency of the methodologies developed by us using ionic liquids for the synthesis of fused heterocycles 32. Synthesis of quinazoline compounds various methods were reported for the synthesis of oxoquinazolines. Unlimited viewing of the articlechapter pdf and any associated supplements and figures.
One of the most attractive synthetic goals, starting from co 2 is a synthesis of quinazoline 2,41h,3hdiones derivatives, possessing wide application in pharmaceutical industry for the synthesis of an intermediates, drugs and building blocks for biologically active pharmaceutical agents. The ch bond ortho to the amino group in anilines was directly functionalized under metalfree conditions. These sizeexpanded u analogues exhibit fluorescent emission wavelengths that span 155 nm, from 335 to 490 nm. 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. Two new synthesized and characterized quinazoline schiff bases 1 and 2 were investigated for anticancer activity against mcf7 human breast cancer cell line. Review article chemical characteristics, synthetic methods. The rapid synthesis of a variety of organic com pounds under. Niementowski synthesis an overview sciencedirect topics. Acaaddemmiicc ss ciieenncess international journal of. Jcprc5 42 synthesis and characterization of new quinazoline4 3h one schiff bases shetha alzubiady and wijdan amer ibrahim department of chemistry, college of science for women, university baghdad, bagdad, iraq. Design, synthesis and anticonvulsant evaluation of novel 8. Pdf owing to the significant biological activities, quinazoline derivatives have drawn more and.
A new rapid and versatile approach using ionic liquiddmso as a chemical reagent for the synthesis of fused heterocyclic compounds in a highly efficient way is described. Methyl, ethyl, isopropyl, benzyl, tbutyl and phenyl magnesium halides and phenyl lithium also add across the 3, 4 double bond to give the corresponding 4 substituted 3, 4dihydroquinazolines. An efficient synthesis of quinazoline2,41h,3hdione from. An efficient construction of quinazolin43hones under.
The first highly accelerated niementowski reaction of anthranilic acid with some amides or. Any derivative of quinazoline may be described as a quinazoline compound. Synthesis and herbicidal evaluation of triketonecontaining. Synthesis and antioxidant properties of novel quinazoline.
Efficient niementowski synthesis of novel 1 3,10,12tetra. Whether youve loved the book or not, if you give your honest and detailed thoughts then people will find new books that are right for them. In this paper, condensation of 2aminobenzamide 1 with benzoyl chlorides 2 in the presence of sbaprso3h as a heterogeneous and reusable nano catalyst for the synthesis of benzamide derivatives 3 and some quinazolinone derivatives 4 was studied scheme 1. All structured data from the file and property namespaces is. The synergy of combined use of dmso and bronsted acid ionic. All structured data from the file and property namespaces is available under the creative commons cc0 license. Subsequent ring closure with acetic anhydride afford corresponding 1,3benzoxazin4one benzoxazinone which will be treated with different amines to give 43hquinazolinone derivatives. These named traditional reactions were performed using microwave assisted synthesis on samsung domestic microwave, 1. Inspired by the high yields obtained using formic acid, a further study of 43h quinazolinones synthesis, as a possible niementowski reaction, was carried out using different aromatic and heteroaromatic carboxylic acid, amine and carboxylic acid were mixed and irradiated under microwaves to yield 2,3disubstituted43h quinazolinones 1al. It is a mancude organic heterobicyclic parent, a member of quinazolines, an azaarene and an orthofused heteroarene. Niementowski quinoline synthesis wikipedia niementowski quinazoline synthesis wikipedia. The synthesized 4chloroquinazolines were generally prepared from anthranilic acid derivatives through the niementowski quinazoline synthesis according to established 55 methods21,22 with the exception of 4b which was prepared via the route shown in figure 8.
Synthesis of some novel quinazoline derivatives having. Design, synthesis and antiinfluenza a virus activity of. Whereas the application of the niementowski reaction to 353 yielded only. Review article chemical characteristics, synthetic methods, and biological potential of quinazoline and quinazolinone derivatives mohammadasif department of pharmacy, grd pg institute of management and technology, dehradun, uttarakhand, india. Synthesis of some new quinazolinone derivatives and. Fourcomponent quinazoline synthesis from simple anilines. Journal of chemical and pharmaceutical research, 20, 57.
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