Which are further treated with hydrazine hydrate using ethanol to get their respective substituted 2mercapto benzoxazole derivatives. Synthesis and characterization of oxazolopyridine and. When the effervescence ceased, the precipitate obtained was filtered and washed with water. Benzoxazole and benzimidazole derivatives were also synthesized by these novel catalysts via the onepot condensation from reaction orthoester with o. An experimentally simple, general, efficient, and ligandfree synthesis of substituted benzimidazoles, 2aminobenzimidazoles, 2aminobenzothiazoles, and benzoxazoles via intramolecular cyclization of obromoaryl derivatives is catalyzed by copperii oxide nanoparticles in dmso under air. Pelagia research library synthesis and characterization of. Synthesis and antimicrobial activity of benzoxazole derivatives. Novel 2substituted phenylbenzimidazole derivatives with. Condensation of aminophenols with carbon disulfide in ethanol using potassium hydroxide as catalyst gave the required benzoxazole thiol in one step.
Predicted possible mechanism for synthesis of substituted benzoxazole derivatives starting from substituted onitro phenols and substituted aldehydes. An efficient strategy for the synthesis of various 2mercaptobenzothiazole derivatives proceeds from ohaloaniline derivatives and carbon disulfide via a tandem reaction in the presence of 1,8diazabicyclo5. These ionic liquids are in the solid state at room temperature and the synthesis is carried out via the onepot condensation reaction of various ophenylenediamine with 1,2diketone derivatives. Benzoxazole is an important class of heterocycle having a bicyclic structure in which an aryl ring is fused with the d site of an oxazole moiety. A highly efficient, simple and rapid method for the preparation of various 2aminobenzoxazoles and other benzoxazole derivatives using a catalytic amount of poly ethylene glycolbound sulfonic acid pegso 3 h is described. Radheshyam shelkar, sachin sarode, jayashree nagarkar. Pdf on jan 1, 2020, kamiar zomorodian and others published synthesis and antifungal activity of benzoxazole derivatives with their sar analysis by sasmap find, read and cite all the research. In addition, the benzothiazole ring is present in various marine or terrestrial natural compounds, which have useful biological activities.
The method to synthesize the designed benzoxazole derivatives is given in scheme 1. Initially, 2chloromethyl1hbenzod imidazole i was synthesized by the reaction of ortho phenylenediamine, chloroacetic acid and hydrochloric acid. Facile and efficient synthesis of benzoxazole derivatives using novel. Phosphorus, sulfur, and silicon and the related elements 2004, 179 2, 305319. Almost all amidino derivatives showed noticeable antiproliferative effect on several tumor cell lines while cyano derivatives showed considerably less pronounced activity due to poor solubility in aqueous cell culture 31,32. A green and efficient protocol for the synthesis of. A series of some novel benzoxazoles were synthesized and evaluated for anti. The heterogeneous catalyst can be recovered and recycled.
It is a mancude organic heterobicyclic parent and a member of 1,3benzoxazoles. To our delight, the optimized analogue 1d showed comparable antiproliferative activity in vitro with better solubility, compared with 1a. Benzimidazole, benzoxazole and benzothiazole derivatives as 5ht2b receptor ligands. The anticancer evaluation of synthesized compounds was carried out by the authors kr, saas, sml and vm. Facile and efficient synthesis of benzoxazole derivatives. Our team of scientists has experience in all areas of research including life science, material science, chemical synthesis, chromatography, analytical and many others.
Benzoxazoles can be considered as structural isosteres of the. Synthesis and evaluation of new benzoxazole derivatives as. The invention provides novel 5 and 6benzoxazolyl alkanoic acids, optionally substituted in the 2position, and derivatives thereof which possess anti. Synthesis and characterization of new 1, 2, 4 triazine thio benzoxazole derivatives mohammad r. Novel benzothiazole, benzimidazole and benzoxazole. Design, synthesis and biological evaluation of benzimidazole. Synthesis of imidazolinone and benzoxazole derivatives, and. The two step conversion of the benzoxazole, first into the benzoxazolium bromide 123 followed by ring expansion afforded the nformyl benzoxazocine 124 scheme. Aug 12, 2018 the designing, synthesis, antimicrobial activity and spectral analysis of the prepared benzoxazole derivatives was done by the authors bn, sk and st.
Synthesis, antimicrobial and cytotoxic activity of 2azetidinone derivatives of pyridyl benzimidazoles. Synthesis, antifungal activities and molecular docking. Benzoxazole is used primarily in industry and research, and has no household use. Synthesis and antimicrobial activity of benzoxazole derivatives 3 rd international conference on past and present research systems of green chemistry september 1921, 2016 las vegas, usa. Nano ceria catalyzed synthesis of substituted benzimidazole, benzothiazole, and benzoxazole in aqueous media. Synthesis and pharmacological screening of some noval. Synthesis of piperazinylsubstituted oxazolopyridine and benzoxazole was achieved in three steps starting from aminophenol and carbon disulfide.
Acetyl derivatives 4 and 6 were prepared by acetylation of compounds 3 and 5 with acetic anhydride. It is found within the chemical structures of pharmaceutical drugs such as flunoxaprofen. The parent benzoxazole scaffold has a planar geometry and is found to be a constituent of several naturally occurring molecules. Five 3,4,5trimethoxyphenyl benzoxazole derivatives iiiaiiie were synthesized and evaluated for their antibacterial and antiinflammatory activity.
An efficient synthesis of benzimidazole derivatives were prepared by wide range of aldehydes and substituted ophenylenediamines by using versatile organocatalyst lproline in an aqueous media at. Also provided is a process for preparing such compounds by cyclising an appropriately substituted oaminophenol and, if necessary, converting the resultant benzoxazole to the desired compound. Synthesis of benzoxazole sulfanilamide derivatives springerlink. Aug 25, 2019 design, synthesis, molecular docking, and anticancer activity of benzoxazole derivatives as vegfr. Jcprc5 2988 synthesis, characterization and biological evaluation of benzoxazole derivatives a p.
Synthesis and characterization of some benzoxazole derivatives sunila t. Benzoxazole and its derivatives like 2aminobenzoxazole find extensive therapeutic importance in medicine for indications such as neural disorders wang et al. Bhatt 2 1research scholar jodhpur national university, jodhpur342003, rajasthan, india 2l. Satyanarayana peruric adepartment of chemistry, chalapathi institute of engineering and technology, guntur, india. Synthesis of some novel quinazoline derivatives having anticancer activity. Antitumor evaluation of some novel cyano and amidino benzothiazole derivatives 1.
Journal of chemical and pharmaceutical research, 2015, 79. Mohsin department of chemistry, college of science, baghdad university, baghdad, iraq abstract this research, involved a series of some new compounds containing different heterocyclic atoms, through. In reference to scheme 3, all compounds table 4 are known and widely used for scaffold synthesis. Synthesis, characterization and biological evaluation of. The pasty mass obtained was diluted with 50ml of water and treated with aqueous sodium bicarbonate solution. Synthesis and characterization of new 1, 2, 4 triazine. A series of imidazolinone and benzoxazole derivatives 3 and 5 have been synthesized by condensation of oxazolinone derivatives 2ac with aniline and 2hydroxyaniline. Biologically active benzoxazole derivatives have been known for long time, since benzoxazoles can be considered as structural isosteres of the naturally occurring. Synthesis of benzoxazole derivatives as interleukin6. All authors read and approved the final manuscript. Synthesis of some novel quinazoline derivatives having anti.
Helby department of pharmaceutical chemistry, faculty of pharmacy, al. Synthesis, antifungal activities and molecular docking studies of benzoxazole and benzothiazole derivatives bo luo 1,2, ding li 2, anling zhang 2 and jinming gao 2, 1 college of life sciences, xinyang normal university, tea plant biology key laboratory of henan province, xinyang 464000, china. Although benzoxazole itself is of little practical value, many derivatives of benzoxazoles are commercially important. Synthesis and pharmacological screening of some noval benzoxazole derivatives shivendra pratap singh, navneet kumar verma, praveen kumar rai and ashok kumar tripathi kailash institute of pharmacy and management, gida, gorakhpur, u. Pdf on jan 1, 2020, kamiar zomorodian and others published synthesis and antifungal activity of benzoxazole derivatives with their sar analysis by. Benzoxazole is an aromatic organic compound with a molecular formula c 7 h 5 no, a benzenefused oxazole ring structure, and an odor similar to pyridine. Pdf synthesis of some novel benzoxazole derivatives and their.
Efficient onepot synthesis of benzoxazole derivatives catalyzed by zinc triflate srinivasulu raminenia, ravi kumar kannasanib and v. Disclosed is a process for preparing 2,5dicarbonamido phenol compounds comprising a step employing a 2alkyl6nitro benzoxazole to form a 2alkyl6amino benzoxazole in which the 2alkyl group is unbranched at the a carbon. Efficient onepot synthesis of benzoxazole derivatives. A highly efficient, simple and rapid method for the preparation of various 2 aminobenzoxazoles and other benzoxazole derivatives using a catalytic amount of. Benzoxazoles as novel herbicidal agents wiley online library.
The synthesized benzoxazole compounds were confirmed by ir, 1hcnmr, mass and screened for their in vitro antimicrobial activity against. Being a heterocyclic compound, benzoxazole finds use in research as a starting material for the synthesis of larger, usually bioactive structures. Synthesis and preliminary pharmacological evaluation. A new series of benzoxazole analogues was synthesized and checked for their in vitro antibacterial, antifungal and anticancer. Based on these findings, a series of benzoic acid substituted benzoxazole were synthesized by refluxing cs 2 and oaminophenol. Synthesis of benzoxazole sulfanilamide derivatives.
A number of hitherto undescribed 2paminobenzenesulfamide benzoxazoles are prepared by treating 2aminobenzoxazole or its 6substituted compounds with p. Among 16 synthetic derivatives of benzoxazole, the compounds 4, 6, 11, 15, 17, and 19 showed a strong suppressive activity against il6induced phosphorylation of signal transducer and activator. Based on this result, the replacement of the benzothiazole scaffold with benzimidazole and benzoxazole moieties afforded 1f and 1g, whose activities were fundamentally retained. Biologically active benzoxazole derivatives have been known for long time, they are the isosteres of cyclic. A series of benzoxazole and derivatives of heterocyclic bearing nitrogen, oxygen and oxazole moieties constitutes the core structure of a several biological active compounds. Synthesis, characterization and biological study of new benzoxazole. This approach was also successfully applied to the synthesis of nformyl benzo 1,4thiazocine from the benzothiazole scheme 16, section 14. Design and synthesis of 2substituted54trifluoromethylphenylsulphonamido benzoxazole derivatives as human gst p11 inhibitors tugba ertanbolellia, kayhan bolellia, yaman musdalb, ilkay yildiza, esin akiyalcina. Reaction of compound 5 with chloroacetyl chloride produced chloroacetyl derivative 7. Application of sbaprso3h in the synthesis of benzoxazole derivatives. Benzoxazole finds use in research as a starting material for the synthesis of larger bioactive structures. Consequently, developing new methodologies for construction of benzoxazole. A simple, green, and efficient method enables the synthesis of benzoxazoles and benzothiazoles from oaminothiophenols and aldehydes using samarium triflate as a reusable acid catalyst under mild reaction conditions in aqueous medium.
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