Selective oxidative decarbonylative cleavage of unstrained. The reaction of 2hydroxyheptadecanoyl chloride 2 and anthranilic acid gave 21hydroxyheptadecyl4h3,1benzoxazin4one 3 which was used as starting material to synthesize some condensed and noncondensed heterocyclic. Structures of the newly synthesized compounds were established by elemental analysis and spectral data. Onepot synthesis of 2substituted 4 h 3,1benzoxazin4. Journal of chemical and pharmaceutical research, 20, 57. Microwave assisted synthesis and analgesic screening of some thiazolyl quinazolinone pritam p. This work was triggered by an undesired finding that treatment of 2chloro5fluoro3nitrobenzoic acid 1a with n cyanopyrrolidine according to method b scheme 1 afforded the expected compound 2a only in 18% yield along with benzoylurea 3a and benzamide 5 as byproducts scheme 3. Then the refluxed mixture was poured into crushed ice.
Onepot synthesis of 2substituted 4h3,1benzoxazin4one. Benzoxazine is composed of an oxazine ring, a heterocyclic aromatic sixmembered ring with oxygen and nitrogen, attached to a benzene ring. This observation have led us to synthesize the structurally related. Synthesis and bioassay studies of benzoxazin4one and. The antibacterial and antifungal activity was evaluated for a number of these products with the intension of producing novel products that. A new and effective onepot method for the synthesis of 2substituted 4h3,1benzoxazin4one derivatives is described in this paper. The 2phenyl1,34hbenzoxazin4one 3 compound was used for the 2 benzoylamino. This method has also been applied for the high yield preparation of 2thioxo3,4dihydro2h1,3. In this paper, we report the synthesis and characterization of 4h3,1benzoxazin4one and quinazolin4imine compounds 1. According to the reaction of 2 4 bromophenyl 4h 3,1. Synthesis of quinazolines benzoyl chloride iii a mixture of appropriate. Onepot synthesis of 2substituted 4 h 3,1benzoxazin4one. Synthesis and antimicrobial activity of newer quinazolinones 99 synthesis of 6 bromo 2 alkylaryl 3 phenyl phenyldiazenyl methylene amino quinazoline 43h one 5. Pdf a series of 2,3disubstituted1,3benzoxazin4one derivatives has been synthesised via the reaction of salicylic acid with various primary amines.
Osyanin and others published synthesis of 1,2,4triazolo5,1 b1,3benzoxazines find, read and cite all the research you need on researchgate. Cheminform is a weekly abstracting service, delivering concise information at a glance that was extracted from about 100 leading journals. The resulting compounds after treated with hydrazine hydrate were proposed to be quinazolin4imine compounds based on the data analyzed from atr and 1h nmr spectrum. The derivatives of 2substituted 4h3,1benzoxazin4one belong to a significant category of heterocyclic compounds, which have shown a wide spectrum of medical and industrial applications. Mostly medicines used are racemic modifications of two enantiomers and sideeffect of these medicines is being found due to presence of the vestigial enantiomers 8,9. Synthesis characterization and antibacterial, antifungal. The resultant solid was filtered, washed with water, dried and recrystallized by using ethanol. Synthesis and biological activity of certain mannich bases. The excess of solvent was then distilled off, and the resulting solid was dried and recrystallised from ethanol, m. Synthesis and reactions of 24 bromophenyl 4h3,1benzoxazine section aresearch paper eur.
Molecules free fulltext asymmetric synthesis of 4,1. Analysis, synthesis, and design of chemical processes fourth edition richard turton richard c. The uses of 2ethoxy4h3,1benzoxazin4one in the synthesis of. Synthesis and fungicidal activity of 1carbamoylmethyl2. Shaeiwitz debangsu bhattacharyya upper saddle river, nj boston indianapolis san francisco new york toronto montreal london munich paris madrid capetown sydney tokyo. Girija department of pharmaceutical chemistry, mother theresa post graduate and. Design and synthesis of novel platelet fibrinogen receptor antagonists with 2 h1,4benzoxazine34 hone scaffold. Synthesis of 1,3benzoxazine4one derivatives using salicylamide 1 mmol and aldehydes 1 mmol catalyzed by h 3 pw 12 o 40 5 mol% in h 2 oetoh 5. Short protecting groupfree syntheses of camptothecin and 10hydroxycamptothecin using. Synthesis and antimicrobial activity of newer quinazolinones. Synthesis of 2methyl35phenyl1,3,4oxadiazole2ylquinazoline43hone 2 anthranilic acid 0.
By using the iminium cation from a mixture of cyanuric chloride and dimethylformamide as a cyclizing agent, a series of 2substituted 4h3,1benzoxazin4one derivatives was synthesized in high yield under mild conditions and simple workup. Synthesis and in vitro anti tumor activity of some novel 2, 3disubstituted quinazolin 43hone derivatives. Asymmetric synthesis is acquiring greater significance in pharmaceutical industry because of the wider application of enantiopure drugs. A mixture of nbenzoyl anthranilic acid and acetic anhydride was condensed to form 2phenyl3,1benzoxazine4one and various 4substituted anilines were condensed with sodium cyanide to form 4substituted phenyl ureas.
Synthesis, antiviral and cytotoxic activities of 22. Synthesis and potential antibacterial activity of some 1,3benzoxazin4one derivatives article pdf available in acta pharmaceutica 503. Benzoxazines heterocyclic building blocks sigmaaldrich. Synthesis, characterization and antimicrobial studies of 3. Tetrahedron letters vol 56, issue 32, pages 46434720 5. Onepot synthesis of 2substituted 4h3,1benzoxazin4one derivatives under mild conditions using iminium cation from cyanuric chloride. Melting points were determined using open ended capillary tube method and are uncorrected. Benzoxazine and their derivatives have been shown to possess a wide spectrum of biological activities. This is partly because of its structure possess wide range of reaction and being derived from anthranilates with various esters, isotoicanhydride and anthranilamide. Synthesis and antimicrobial evaluations of new bioactive dyes and their cyclized derivatives synthesized from 4,5,6,7tetrahydrobenzobthiophene 618628 en 223. A series of 2substituted 4h3,1benzoxazine4one formulae 2ai was prepared in good yield at room temperature using anthranilic acid and nine different derivatives of acyl chloride and benzoyl chloride as starting materials as well as iminium cation as cyclizing agent in dimethylformamide in the presence of triethylamine table 1. The reaction of 3,2benzoxazin4ones with different nitrogen containing reagents, was successfully used.
Volume 56, issue 32, 5 august 2015, pages 46834685. Synthesis and in vitro anti tumor activity of some novel 2. The uses of 2ethoxy4h3,1benzoxazin4one in the synthesis of some quinazolinone derivatives of antimicrobial activity. There are several benzoxazine derivatives depending on the position of the oxygen and nitrogen in the ring. A facile and efficient synthesis of 4h1,3benzoxazine4. These properties are more fully detailed in the supplementary material. The results of synthesis of 2ethoxy4h3,1benzoxazin4ones show. Guanidinum chloride as dehydrocyclization agent in the. Elemental analysis of given compounds were carried out, percentage of elements, c, h, n are recorded at orchid chemicals and pharmaceutical ltd.
To access a cheminform abstract of an article which was published elsewhere, please select a full text option. The original article is trackable via the references option. A new series of 2,3disubstituted quinazolin43hone derivatives was synthesized via nucleophilic attack at c2of the corresponding key starting material 24. Fs college of pharmacy ahmednagar, hod of pharmaceutical chemistry department 1department of pharmaceutical chemistry, ideal college of pharmacy and research kalyan. Research article open access onepot synthesis of 2. From both spectra it showed that the synthesis of targeted compound, 4h3,1quinzolin4one was unsuccessful. Pdf a new method has been designed to prepare the known benzoxazinone derivative 2nphthaloylmethyl4h3,1benzoxazin4one 4. Synthesis and anti hiv1 activity of some novel clubbed hetrocycle compounds dr. The most notable being antibacterial and antihelmentic properties 110. Synthesis and biological activity of certain mannich bases 55 refrigerator overnight. Highly efficient and mild cascade reactions triggered by.
In this work, we developed simple general procedures for the synthesize of nbenzyl carbamothioyl2hydroxybenzamides, 20, and 21, nbenzyl carbamoyl2hydroxysubstitutedbenzamides 23, and 2benzyl aminosubstituted1,3benzoxazin4one 15 and 26. Us5071850a us07403,757 us40375789a us5071850a us 5071850 a us5071850 a us 5071850a us 40375789 a us40375789 a us 40375789a us 5071850 a us5071850 a us 5071850a authority us unite. A simple synthesis of 2substituted4h3,1benzoxazin4ones by. The main objective of this investigation is to synthesis and study the inhibitive effect of 2pentadecylquinazolinylthiourea pqt for the carbon steel surface in hydrochloric acid solution using potntiostate polarization method. Pdf synthesis and potential antibacterial activity of some 1,3. Pdf design and synthesis of novel platelet fibrinogen. The synthesis of a novel series of substituted 2phenyl4 h3, 1. Control experiments and density functional theory dft calculations suggest that the reaction involves a 1,5h. Excess of acetic anhydride was distilled off under reduced pressure. Abstract an efficient, mild and novel method is described for onepot conversion of stable triisopropylsilyl and tertbutyldimethylsilyl carboxylates to their corresponding acyl or aroyl isothiocyanates using insitu generation of ph3pscn2 at room temperature under neutral condition. A facile and efficient synthesis of 4h1,3benzoxazine4one with electronwithdrawing group derivatives. Studies on some benzoxazine4one derivatives with potential biological activity. Cyclocarbonylation of oiodoanilines with acid chlorides. The 2phenyl1,34hbenzoxazin4one 3 compound was used for the 2benzoylamino.
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