Niementowski quinazoline synthesis pdf merge

Reactions in the presence of solvent and solventfree synthesis can be realised. The original conditions for this transformation, however, proved somewhat limiting as they required extended heating at. The present procedure can provide efficient synthetic methods for the formation of both 2substituted and 2,3disubstituted quinazolin4one rings depending on the use of easily available starting. Synthesis of nheterocycles benzofused nheterocycles synthesis of quinazolines. It is an aromatic heterocycle with a bicyclic structure consisting of two fused sixmembered aromatic rings, a benzene ring and a pyrimidine ring, it is a light yellow crystalline solid that is soluble in water. Quinazoline and quinazolinone are reported for their diversified biological activities and compounds with different substitutions bring together to knowledge of a target with understanding of the molecule types that might interact with the target receptors. 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. 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. A transitionmetalfree synthesis of quinazolin4ones by cs2co3promoted snar reaction of orthofluorobenzamides with amides followed by cyclization in dimethyl sulfoxide has been developed. Using 2amino6fluorobenzonitrile, an s n ar reaction with a protected amino alcohol afforded the key starting material 1a in a modest yield.

The niementowski quinazoline synthesis is the chemical reaction of anthranilic acids with amides to form 4oxo3,4dihydroquinazolines 3hquinazolin4ones. Niementowski synthesis an overview sciencedirect topics. Implication of quinazoline 43hones in medicinal chemistry. Cn104016929b a kind of method of synthesis quinazoline4. A simple and efficient approach for the synthesis of 2. The invention provides a kind of method of synthesis quinazoline4 3hone heterogeneous ring compound, reaction expression is as follows, wherein r 1 for substituting group, can be h, f, no 2, alkyl, or alkoxyl group. A highly employed method for 43hquinazolinone synthesis is based on acylation of anthranilic acid with acyl chloride.

The niementowski quinoline synthesis is the chemical reaction of anthranilic acids and ketones or aldehydes to form. Niementowski quinazolinone synthesis, named after its discoverer. The quinazoline group could be partassembled via a number of reported 43hquinazolinone syntheses24,25 such as the niementowski reaction. Wo2008125867a2 process for the preparation of gefitinib. The highly accelerated niementowski synthesis of quinazolin43hone and. Microwave assisted synthesis and molecular docking studies. The first known synthesis of quinazoline was reported in 1895 by august bischler and lang through the decarboxylation of the 2carboxy derivative quinazoline 2carboxylic acid. Biological activities of quinazolines diverse biological activities were attributed to compounds possessing a quinazoline ring system. Quinazoline is a organic compound with the formula c 8 h 6 n 2. An efficient construction of quinazolin43hones under. Chemical characteristics, synthetic methods, and biological. The niementowski quinazoline synthesis is the chemical reaction of anthranilic acids with amides to form 4oxo3, 4dihydroquinazolines.

Research has demonstrated that the niementowski quinazoline synthesis could be employed for. It is an aromatic heterocycle with a bicyclic structure consisting of two fused sixmembered aromatic rings, a benzene ring and a pyrimidine ring. A sustainable synthesis of quinazoline and 2aminoquinoline via acceptorless dehydrogenative annulation is catalyzed by earthabundant welldefined manganese complexes bearing nns ligands. It is an aromatic heterocycle with a bicyclic structure consisting of a two fused sixmembered aromatic rings, a benzene ring and a pyrimidine ring. The last two decades have brought new approaches to the synthesis of pyrrolo1,2a quinazoline framework and thus their. Synthesis of some novel quinazoline derivatives having anticancer activity. Synthesis of two bifunctional ligands for the quest threehybrid system. Here we describe the synthesis of new pyrido3,4g quinazoline derivatives and the evaluation of the inhibitory potencies of these compounds toward cdk5, ck1, gsk3, clk1 and dyrk1a. A nickelcatalyzed sequential dehydrogenation and condensation process enables a sustainable synthesis of a wide range of polysubstituted quinolines from. Owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. Also known as 1,3diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. Results and discussion the first step in this reaction involved the synthesis of pyrido2,3dpyrimidin4ones 2 which took place by reacting 2amino4,6disubstitutednicotinonitriles 1 with formic acid. The highly accelerated niementowski synthesis of quinazolin43hone and quinazolin2,4dione derivatives under microwave irradiation is reported.

Quinazolinone and its derivatives possess a large class of biologically active. Desai department of chemistry, veer narmad south gujarat university, surat395007, india email. Quinazolin4ones with 2, 3disubstitution is reported to. Quinazoline is an organic compound with the formula c 8 h 6 n 2. A niementowskitype cyclisation of 1a in a mixture of formic and sulfuric acid at reflux afforded 2a in sufficient yield to attempt the. The pasty mass obtained was diluted with 50ml of water and treated with aqueous sodium bicarbonate solution. Syhthesis following methods were reported for the synthesis of oxoquinazolines. It is a light yellow crystalline solid that is soluble in water. The use of oxygen as an oxidant combined with the transitionmetal, additive and solvent. Abstract the thermal transformation of an anthranilic acid into 4. Reacting the catalyzer used is mantoquita, can be cuprous iodide, cuprous chloride, red copper oxide, cuprous acetate etc.

These named traditional reactions were performed using microwave assisted synthesis on samsung domestic microwave, 1. Stefan niementowski zjovkva, 4 augustus 1866 warschau, juli 1925 was een pools scheikundige. Pdf new pyrido3,4gquinazoline derivatives as clk1 and. Synthesis of some new quinazolinone derivatives and. Synthesis of quinazoline compounds various methods were reported for the synthesis of oxoquinazolines. Niementowski quinoline synthesis wikipedia niementowski quinazoline synthesis wikipedia. Efficient niementowski synthesis of novel 1 3,10,12tetra. Synthesis and reactivity of some novel quinazoline. Quinazoline derivatives with antitubercular activity. An expedient synthesis of oxazepino and oxazocino quinazolines.

There is also provided a process for preparing a compound of formula xl comprising converting a compound of formula x to the compound xl. Various methods were reported for the synthesis of oxoquinazolines. Reacting the catalyzer used is mantoquita, can be cuprous iodide, cuprous chloride, red copper oxide. Page 98 general papers arkivoc 2005 xiii 98108 niementowski reaction. The synergy of combined use of dmso and bronsted acid. Synthesis, biological evaluation and molecular docking of. Quinazoline and condensed quinazoline exhibit potent central nervous system cns activities like antianxiety, analgesic, antiinflammatory 10and anticonvulsant 11. Niementowski was een voornaam scheikundige in zijn tijd. Subsequent ring closure with acetic anhydride afford corresponding 1,3benzoxazin4one benzoxazinone which will be treated with different amines. Rutaecarpine figure 1 shows a variety of pharmacological activities including. Pdf most of the drugs and pharmacologically relevant molecules possess heterocyclic.

It has been applied to substitute quinozolines, for the preparation of 6,7dimethoxy quinazoline through the intermediate 6nitroveratradehyde. Review article chemical characteristics, synthetic methods. Pyrrolo1,2aquinazolines are tricyclic compounds with great potential and combine the. Pdf pyrrolo1,2aquinazolines have raised some interest as. Microwaves in drug discovery and multistep synthesis. The quinazoline group could be partassembled via a number of reported 43hquinazolinone syntheses24, 25 such as the niementowski reaction.

There is provided a compound of formula iii, and a process for preparing a compound of formula v comprising converting a compound of formula iii to the compound v, wherein x is fluoro, chloro, bromo or iodo. Synthesis of some novel quinazoline derivatives having. This strategy allows the use of both primary as well as secondary. Niementowski quinazoline synthesis, cheminform on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Stephen j baker, steven m firestine, david smithrud, frank salinas, stephen j benkovic. When the effervescence ceased, the precipitate obtained was filtered and washed with water. Molecular iodine catalyses a benzylic sp 3 ch bond amination of 2aminobenzaldehydes and 2aminobenzophenones with benzylamines to provide quinazolines in very good yields. 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. In 1903, siegmund gabriel reported the synthesis of the parent quinazoline from onitrobenzylamine, which was reduced with hydrogen iodide and red phosphorus to 2aminobenzylamine. Rutaecarpine type alkaloids constitute an important class of indolopyridoquinazolinone heterocycles, which belong to the subgroup of quinazoline type alkaloid, belonging to rutaceae family 1. The usual synthesis of quinazolines make use of an odisubstituted benzene structure from which the quinozoline.

Compared to the conventional conditions, this new method shows the advantages of a good substrate tolerance, and a clean and rapid conversion. This method offers the advantages of proceeding in neutral conditions, giving high to excellent isolated yields 8392% for niementowski synthesis with easy workup procedure. The invention provides a kind of method of synthesis quinazoline 4 3hone heterogeneous ring compound, reaction expression is as follows, wherein r 1 for substituting group, can be h, f, no 2, alkyl, or alkoxyl group. The current reaction is a variant of the classical niementowski quinazoline synthesis, which involved the cyclocondensation of an nalkylamide with anthranilic acid 11. The thermal transformation of an anthranilic acid into 4.