More than three fourth of the bioactive drugs available in the market are all hetero cycles. To discover new triketone herbicides with broadspectrum weed control as well as excellent crop selectivity, a series of total 52 novel triketonecontaining quinazoline2,4dione derivatives were synthesized and further bioevaluated. The synthesis of various congeners took place via a niementowski condensation, inspired by alexandre and coworkers. The pasty mass obtained was diluted with 50ml of water and treated with aqueous sodium bicarbonate solution. Synthesis of quinazolinones and quinazolines request pdf. Synthesis, characterization and biological screening of quinazoline4one analogs introduction hetero cyclic chemistry research reached in all areas of drug discovery in recent days. Synthesis, characterization, and anticancer activity of. The use of oxygen as an oxidant combined with the transitionmetal, additive and solventfree.
Compounds 1 and 2 demonstrated a remarkable antiproliferative effect, with an ic 50 value of 6. A total of 22 quinazoline thioether derivatives incorporating a 1,2,4triazolo4,3apyridine moiety were designed, synthesized, and evaluated as antimicrobial agents in agriculture. Analgesics, antibacterial and locomotor activity of. 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. Exploring novel 4hydroxyphenylpyruvate dioxygenase ec 1. The synthesized compounds were characterized by spectral methods.
A simple and efficient approach for the synthesis of 2. Facile synthesis of 3substituted quinazoline2,4dione. Design, synthesis and anticonvulsant evaluation of novel 8. Also disclosed are a preparation method therefor, an intermediate, a pharmaceutical composition having the quinazoline derivative, and an application thereof.
A series of quinazolinone and benzamide derivatives have been efficiently synthesized in good to excellent yields via the reaction of 2aminobenzamide and aromatic benzoyl chlorides under solventfree conditions using sbaprso3h as a nano solid acid catalyst. Synthesis and properties of quinazoline derivatives. Quinazoline in 1905 riedel obtained a patent describing a synthesis of quinazoline from onitrobenzaldehyde through reaction with formamide to the onitrobenzylidenediformamide. Dribofuranose and by using the silylation method, followed by debenzoylation by methanolic sodium methoxide to afford the corresponding free nnucleosides. Quinine synthesis mystery solved news chemistry world. Synthesis of nheterocycles benzofused nheterocycles synthesis of quinazolines. Subsequent ring closure with acetic anhydride afford corresponding 1,3benzoxazin4one benzoxazinone which will be treated with different amines to give 43hquinazolinone derivatives. Disclosed are as represented by formula i a quinazoline derivative and a pharmaceutical acceptable salt thereof, or, an enantiomer, a nonenantiomer, a tautomer, a racemate, a solvate, a metabolic precursor, or a prodrug of both. Palladiumcatalyzed oxidative threecomponent coupling of anthranilamides with isocyanides and arylboronic acids.
Research has demonstrated that the niementowski quinazoline synthesis could be employed for the creation of potential egfrinhibiting molecules. Synthesis and biological evaluation of novel quinazoline derivatives obtained by suzuki cc coupling. Among these compounds, the chemical structure of compound 6l was further confirmed via singlecrystal xray diffraction analysis. This synthesis, which was performed via a rarely described modified niementowski reaction, is a further example of the utility of microwaves in organic synthesis. Media in category organic name reactions the following 200 files are in this category, out of 241 total. A simple, efficient and convenient coppercatalyzed method allows the synthesis of quinoline2carboxylate derivatives through sequential intermolecular addition of alkynes onto imines and subsequent intramolecular ring closure by arylation at room temperature. Nucleosides obtained have been identified by their spectral analysis. Synthesis of some novel quinazoline derivatives having anticancer activity.
It is established for the first time that condensation of 2. Ebscohost serves thousands of libraries with premium essays, articles and other content including synthesis of novel quinazoline4one derivatives and their acyclonucleoside analogs. Journal of chemical and pharmaceutical research, 20, 57. In continuation of our efforts3540, we report here the synthesis of novel 2,4,6trisubstituted quinazoline derivatives, their antibacterial and anticancer activities. Molecular iodine catalyses a benzylic sp 3 ch bond amination of 2aminobenzaldehydes and 2aminobenzophenones with benzylamines to provide quinazolines in very good yields. All structured data from the file and property namespaces is available under the creative commons cc0 license. Benzoquinazoline nucleus was cyclized in good yield from nprotected naphthylamines using hexamethylenetetramine in tfa and potassium ferricyanide in aqueous ethanolic koh. A simple base functionalized supported ionic liquid phase catalyst using 1hexyl3methyl imidazolium hydroxide ionic liquid supported on silica, hmimohsio 2 was used as an efficient, heterogeneous catalyst for the synthesis of quinazoline2,41h,3hdiones motif through the carboxylative coupling of co 2 with 2aminobenzonitriles. Facile solid phase synthesis of 1,2disubstituted6nitro. A new series of 8substituted43hquinazoline 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. Efficient niementowski synthesis of novel 1 3,10,12tetra.
Synthesis of some novel quinazoline derivatives having. The reaction enables great flexibility of the substitution patterns on quinazolines and is applicable to two different nitriles to give a regioselective product. The bioactive assays showed that most of the compounds exhibited moderate antimicrobial activities against the tested strains. Two new synthesized and characterized quinazoline schiff bases 1 and 2 were investigated for anticancer activity against mcf7 human breast cancer cell line. A simple and efficient approach for the synthesis of 2aminoquinazoline derivatives in moderate to good yields. An efficient synthesis of quinazoline2,41h,3hdione.
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. The use of oxygen as an oxidant combined with the transitionmetal, additive and solvent. Alkylation of 2substituted quinazolin4ones with cymantrenylalkyl bromides on using k 2 co 3, potassium tertbutoxide, and sodium hydride as bases has been studied. The synthesis of new quinazoline derivatives with 2,3 and 4positioned cymantrenyl fragment is described. Owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. Heres an entire list but learning all this is too much a abramovitchshapiro tryptamine synthesis acetalisation acetoacetic ester condensation achmatowicz reaction acylation acyloin condensation adams catalyst adams decarboxylation. A highly employed method for 43hquinazolinone synthesis is based on acylation of anthranilic acid with acyl chloride. Synthesis, characterization and antimicrobial studies of. Synthesis and biological evaluation of novel quinazoline.
A novel synthetic pathway to benzoquinazolines from naphthylamines is reported. Efficient niementowski synthesis of novel derivatives of 1. Chun qian, kui liu, shouwei tao, fangling zhang, yongming zhu, shilin yang. This method is efficient and convenient with respect to previously reported synthetic pathways. Syhthesis following methods were reported for the synthesis of oxoquinazolines. One of the binding interactions between the inhibitor and the active site is a hydrogen bond to a water molecule, which acts as a hydrogenbonding bridge to two tyrosine residues. Us chemists have reproduced a 90year old experiment to settle a 50year old controversy. 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. Two organic chemists claim to have settled a major dispute over the first synthesis of quinine by revisiting an experiment performed over 90 years ago. This type of reaction provides an alternative approach for the formation of cc, cb, and csi bonds. Facile solid phase synthesis of 1,2disubstituted6nitro1,4 dihydroquinazolines using a tetrafunctional scaffold xiaobing wang, aimin song, seth dixon, mark j. The bioassay results revealed that some of the compounds possessed noticeable in. When the effervescence ceased, the precipitate obtained was filtered and washed with water. Compounds with promising activity have been identified.
The synergy of combined use of dmso and bronsted acid. 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. A bottomup approach to monodisperse nanostructures aibin shi a, megh raj pokhrel a,b, stefan h. An efficient onepot approach to multiple substituted quinazolines with diaryliodonium salt 1, and two nitriles 2 has been presented. In this paper the onestep synthesis of the novel pyrido2,3. 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. Synthesis and reactivity of some novel quinazoline. Bossmann a a kansas state university, department of chemistry, 111 willard hall, manhattan, ks 665063701, usa. 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. The thermal transformation of an anthranilic acid into 4. Synthesis of novel quinazoline4one derivatives and their. Files are available under licenses specified on their description page.
The quinazoline structure shown is an inhibitor of the enzyme scytalone dehydratase. Devi and coworkers have reported the synthesis of some new aza isatin derivatives containing 43h quinazolinones. Acid hydrazide, acetylhydrazine carboxylate and acetylhydrazinecarbodithioate were the most active compounds with. Synthesis of highly charged rutheniumiiquaterpyridinium complexes. Concise synthesis of quinazoline alkaloids, luotonins a. Synthesis of some new quinazolinone derivatives and. A series of novel 1methyl3substituted quinazoline2,4dione derivatives was designed, synthesized, and evaluated for their antimicrobial activities against six strains of bacteria and five fungi in vitro. Reduction of this with zinc and dilute acetic acid gave quinozoline in. 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.
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