Pdf the conventional methodology was adopted to synthesize the titled compounds. Efficient catalyst for the synthesis of benzimidazole and benzoxazole derivatives. Efficient conversion of 2thione to 2oxo derivatives. An improved environmentally benign procedure for the synthesis of various benzimidazole and benzoxazole derivatives using green solvent peg400. Pdf benzoxazole and benzothiazole synthesis benzoxazole. An attempt to perform hydrolysis under acidic and basic. A ballmilling strategy for the synthesis of benzothiazole. The synthesis method of the benzoxazole compound is characterized by synthesizing the benzoxazole compound under the mild condition by taking a substituted diphenol compound and primary amine as raw materials, taking copper as a catalyst and taking air as an oxidant. The anticancer evaluation of synthesized compounds was carried out by the authors kr, saas, sml and vm. The synthesis of new hydrazone derivatives 3ag was carried out according to the steps shown in figure 1. In this thesis it was attempted to investigate the synthesis, functionalisation and coordination chemistry of these compound class and finally look at a method of synthesising chiral 4hydroxybenzoxazoles from amino acids.
An update on the synthesis of benzoxazoles semantic scholar. Different derivatives of 3 benzoxazole 2yl4phenyl4hchromene2amine bc 1bc 6. In the current research work, the title compounds 2mercaptonsubstituted arylidine benzoxazole 5carbohydrazide derivatives were synthesized by the reaction of schiff bases of 2mercapto benzoxazole 5carbohydrazide with appropriate aromatic aldehydes. Synthesis, molecular docking and antimicrobial evaluation. Department of chemistry, faculty of science, banaras hindu university, varanasi 221 005, india. Synthesis and antimicrobial activity of novel 2substituted benzimidazole, benzoxazole and benzothiazole derivatives. Synthesis of benzoxazole and benzothiazole derivatives of nprotected amino acids is also shown in the solution phase. The invention provides a synthesis method of a benzoxazole compound. Synthesis, antifungal activities and molecular docking. Table 1 the physicochemical properties of synthesized benzoxazole derivatives 126 comp. New benzoxazole derivatives as antiprotozoal agents. New derivatives of benzoxazole, benzothiazole, and benzimidazole. Afshari sharif abad3 1department of chemistry, payame noor university, po box19395469tehran, islamic republic of iran. Synthesis of benzoxazole sulfanilamide derivatives.
Patil college of pharmacy, chopda, maharashtra, india. Preparation of 5,7 dichloro2ethylthio1,3benzoxazole 2. Targets containing the benzoxazole moiety either isolated from plants or accessed by total synthesis have remarkable biological. Rateb a series of benzothiazoles and benzoxazoles was synthesized and screened against two breast cancer cell lines, mcf7 and mda231. Philoppes b apharmaceutical organic chemistry department, faculty of. Benzoxazole, synthesis, antimicrobial, anticancer, characterization. Synthesis and antimicrobial activity of novel 2substituted. Easy, simplistic and green synthesis of various benzimidazole. Saloni kakkar1,sumit tahlan1,siong meng lim2,3,kalavathy ramasamy2,3,vasudevan mani4, syed adnan ali shah2,5and balasubramanian narasimhan1.
A highly efficient, simple and rapid method for the preparation of various 2 aminobenzoxazoles and other benzoxazole derivatives using a catalytic amount of. Acacia concinna pod catalyzed synthesis of 2 arylbenzothiaoxazole derivatives rahul bhat a, shrikrishna karhale a, satyanarayan arde b, vasant helavi a, a department of chemistry, rajaram college, kolhapur 416004, india. Synthesis and anticholinesterase activities of novel glycosyl benzoxazole derivatives yuran wu, shuting ren, lei wang, youxian wang, shuhao liu, weiwei liu, dahua shi, and zhiling cao journal of chemical research 2020 44. An update on the synthesis of benzoxazoles semantic. Antitumor evaluation of some novel cyano and amidino benzothiazole derivatives 1. Therefore, this work deals with the synthesis of the mannich bases of. The synthesis of these compounds was started from substituted phenyl. Consequently, developing new methodologies for construction of benzoxazole. Benzoxazole derivatives have different biological activities. Benzimidazoles have also been prepared on a solid phase.
Benzoxazole derivatives are very useful compounds with well known biological activity. Onepot multicomponent reaction of catechols, ammonium. Jul 01, 2017 general procedure for synthesis of substituted benzoxazole derivatives starting from substituted 2amino phenols and substituted benzoic acids a solution of substituted 2amino phenols 10 mmol was prepared in a mixture of dioxane. We studied the possibility to synthesis of benzoxazoles by the reaction of 2aminophenol and substituted aldehyde using nisio 2 as the catalyst. Condensation of aminophenols with carbon disulfide in ethanol using potassium hydroxide as catalyst gave the required benzoxazole thiol in one step. Biologically active benzoxazole derivatives have been known for long time, they are the isosteres of cyclic nucleotides and easily interact with the biopolymers of the organisms 1. As a result of the cyclization reaction, benzoxazole derivatives bearing an ester group in the c. Authors saloni kakkar 1, sumit tahlan 1, siong meng lim 2 3, kalavathy ramasamy 2 3, vasudevan mani 4, syed adnan ali shah 2 5. Synthesis of compounds 3a3p were performed according to literature methods. Synthesis and pharmacological screening of some benzoxazole. In the initial step, ethyl 25fluorobenzoxazol2ylthioacetate 1 was synthesized via the reaction. Many of tested compounds showed an interesting binding profile. Procedure for synthesis of benzoxazole derivatives 22benzoxazol2ylthio methyl1hbenzimidazol1yl acetohydrazide step 1. Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to uk1.
Similarly, the general synthesis of benzimidazoles is by the condensation reaction of 1,2phenylenediamine with carboxaldehydes, carboxylic acids,6,7 or their derivatives 8,9 such as, chlorides, nitriles, and orthoesters, under strong acidic conditions, with high temperatures. Diversity oriented green synthesis of novel benzoxazole. These compounds possess antimicrobial, central nervous system activities, antihyperglycemic potentiating activity, analgesic, and antiinflammatory activity. Lemon juice as a natural and ecofriendly catalyst has been utilized for the synthesis of benzothiazole and benzoxazole derivatives by the reaction of 2aminothiophenol or 2aminophenol with a variety of aryl aldehydes in goodexcellent yields. General procedure for the synthesis of benzoxazolescompound b1b5 a mixture of thiocyanate a1a5 0. Using this procedure, a wide range of benzoxazoles was successfully synthesized in the. Synthesis and pharmacological screening of some noval. Being a heterocyclic compound, benzoxazole finds use in research as a starting material for the synthesis of larger, usually bioactive structures. An efficient conversion of benzoxazole 2thione to 2one derivative has been achieved in high yield. All authors read and approved the final manuscript.
The formation of suspicious products of bcs derivatives figure 1 was obtained in three steps. Synthesis and characterization of some benzoxazole derivatives. Although various derivatives are reported in the literature for the synthesis and antimicrobial evaluation of benzimidazole, benzoxazole and benzothiazole incorporated in different heterocyclic ring reddy et al. A convenient solventfree method for the synthesis of benzothiazole, benzimidazole, and benzoxazole derivatives has been developed using recyclable znonps via a ballmilling strategy. Benzoxazole, containing a 1,3oxazole system fused with a benzene ring, has a profound effect on medicinal chemistry research owing to its impo. Herein, we report an efficient and environmentally friendly method for the synthesis of benzoxazoles catalyzed by nickel supported silica at room temperature scheme 1. Synthesis and characterization of new 1, 2, 4 triazine.
Phospho sulfonic acid catalyzed synthesis of benzimidazole. Synthesis of benzoxazole derivatives as interleukin6. Aug 12, 2018 procedure for synthesis of benzoxazole derivatives 22benzoxazol2ylthio methyl1hbenzimidazol1yl acetohydrazide step 1. The solvent was removed under reduced pressure and the residue to offer the product. Hence synthesis of biologically active benzoxazole derivatives is a demanding work in the present scenario.
The beneficial features of this new synthetic approach include short reaction time, a clean reaction profile with mild reaction condition and an easy. Synthesis and evaluation of new benzoxazole derivatives as. Based on benzoxazole and benzothiazole scaffold as an important pharmacophore, two series of 2aryloxymethyl benzoxazole and benzothiazole derivatives were synthesized and their antifungal effects against eight phytopathogenic fungi were evaluated. They were tested in radioligand binding experiments to evaluate their affinity for 5ht1a and 5ht2a serotonergic. The designing, synthesis, antimicrobial activity and spectral analysis of the prepared benzoxazole derivatives was done by the authors bn, sk and st. Seventeen derivatives of 2furyl2 benzoxazole and three derivatives of 2thienyl2 benzoxazole, having different substituents in the benzene moiety position 5 and in the furanic or thiophenic. 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 of transcription stat 3 by 8090%. Synthesis of benzoxazole sulfanilamide derivatives springerlink. Anticancer activity of benzoxazole derivative future journal of. The method involves the action of aromatic and heterocyclic selenoamides on some o. Synthesis of benzoxazoles, benzimidazoles, and benzothiazoles. Purification of the peptide was performed by using semipreparative hplc using a linear gradient over 20 min general procedure for the synthesis of benzoxazole derivatives of zlaladlpheglyoh and zlalalpheglyohbocpheoh 1 equiv and onosyloxy 1 equiv were added to a 25 ml roundbottom flask, after that, dipea 1.
Synthesis of 2aceto hydrazide thio benzoxaz ole a2 a mixture of 2chloroacetyl thio benzoxazole a1 22. Novel benzimidazole, benzoxazole and benzothiazole derivatives were designed and synthesized from pn,ndiethyl amino salicylaldehyde with different. Efficient onepot synthesis of benzoxazole derivatives catalyzed by. Synthesis and anticholinesterase activities of novel. Usman1,shaikh tanvery2,sayad imran wahab3 1assistant professor, department of pharmacognosy, smt. Benzoxazole is an aromatic organic compound with a molecular formula c 7h5no, a benzenefused oxazole ring structure, and an odor similar to pyridine. A new class of 5,7dichloro1,3 benzoxazole derivatives 411 were synthesized by fusing 5,7dichloro2hydrazino1,3 benzoxazole 3 nucleus with aliphatic acids, active methylene compounds, and with selected esters to form heterocyclic ring systems like 1,2,4triazoles, pyrazoles, and triazine moieties. Synthesis, characterization and biological evaluation of. In here, compounds 5b, 5d, 5g, 5j, 5k, 5l and 6a6d, 6f6l were synthesized for the. Synthesis of piperazinylsubstituted oxazolopyridine and benzoxazole was achieved in three steps starting from aminophenol and carbon disulfide.
Synthesis of benzoxazole 2ones, benzothiazole2ones and their 2thione derivatives. Easy, simplistic and green synthesis of various benzimidazole and benzoxazole derivatives using peg400 as a green solvent. Pdf synthesis of some novel benzoxazole derivatives and their. In the initial step, ethyl 25fluorobenzoxazol2ylthioacetate 1. It can also be used as starting material for other bioactive molecules. Efficient onepot synthesis of benzoxazole derivatives. The parent benzoxazole scaffold has a planar geometry and is found to be a constituent of several naturally occurring molecules. Fatemeh hakimia,b, mehdi fallahmehrjardia,c, elham. The process is also highly efficient even on a multigram scale and provides easy product.
We describe herein the synthetic method to benzoxazole derivatives via the coppercatalyzed hydroamination of alkynones with 2aminophenols. Synthesis and in vitro antitumor activity of new benzothiazole and benzoxazole derivatives manal m. Phospho sulfonic acid catalyzed synthesis of benzimidazole, benzoxazole and quinoxaline derivatives under green solvent at ambient temperature s. Acacia concinna pod catalyzed synthesis of 2arylbenzothia. Synthesis of new quinolone derivatives linked to benzothiazole or benzoxazole moieties as anticancer and antioxidant agents mohamed a abdelgawad 1,2, phoebe f lamie1 and osama m ahmed3 1pharmaceutical organic chemistry department, faculty of pharmacy, benisuef university, beni suef, egypt. Synthesis, characterization, and study of antibacterial activity of some. A series of new compounds containing a benzimidazole, benzothiazole, or benzoxazole nucleus linked to an arylpiperazine by different thioalkyl chains was prepared.
The reaction scheme is straightforward and efficient. The reactions worked well both in the solution phase and on a resin solid support. Due to these biological activities, the synthesis of benzothiazole is a considerable area of current discussion. Satyanarayana peruric adepartment of chemistry, chalapathi institute of engineering and technology, guntur, india. The synthesis of titled compounds from starting material i. Synthesis of benzoxazole2ones, benzothiazole2ones and. Easy, simplistic and green synthesis of various benzimidazole and. A new class of benzoxazole 2ones, benzothiazole2ones and their 2thione derivatives has been synthesized in onepot protocol. Iranian journal of catalysis 92, 2019, 173179 iranian journal of catalysis acacia concinna pod catalyzed synthesis of 2 arylbenzothiaoxazole derivatives rahul bhata, shrikrishna karhalea, satyanarayan ardeb, vasant helavia, adepartment of chemistry, rajaram college, kolhapur 416004, india. Cn104327008a synthesis method of benzoxazole compound. Synthesis of some new benzoxazole derivatives and investigation of their anticancer activities eur j med chem. Benzoxazoles being structurally similar to bases adenine and guanine interact with biomolecules present in living systems. Pdf benzoxazole and benzothiazole synthesis benzoxazole and. A new series of benzoxazole analogues was synthesized and checked for their in vitro antibacterial, antifungal and anticancer.
Efficient onepot synthesis of benzoxazole derivatives catalyzed by zinc triflate srinivasulu raminenia, ravi kumar kannasanib and v. Facile and efficient synthesis of benzoxazole derivatives. Philoppes b apharmaceutical organic chemistry department, faculty of pharmacy, cairo university, egypt. Procedure for synthesis of benzoxazole derivatives. After that benzothiazole derivatives have been extensively studied and found to have diverse chemical reactivity and broad spectrum of activity 37. Compounds 5a, 5b, 5h, and 5i exhibited significant antifungal activities against most of the pathogens tested. The method affords environmentally friendly reaction conditions that score high on the ecoscale with the low efactor.
In this study, mitsunobu reagent, dead diethyl azodicarboxylate and pph 3, and ethyl. Jun 15, 2017 this study reports that a series of synthetic derivatives of benzoxazole have suppressive effects on il6mediated signaling. Preliminary mechanistic experiments revealed that the reaction would procee. Synthesis of new arylpiperazinylalkylthiobenzimidazole. Synthesis and pharmacological screening of some benzoxazole derivatives as antiinflammatory agents mohammed rageeb mohammed usman,rana sohil d1,md. A simple and efficient method has been developed for the synthesis of benzoxazoles from 2aminophenol and substituted aldehydes in the presence of a. 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. The 5f203 switches on cytochrome p450 cyp1a1 gene expression and thus exhibits anticancer activity. Most importantly, synthesis of benzoxazole derivatives of polypeptides by spps is also demonstrated. New formazan dyes derivatives, derived from 2mercapto benzoxazole. Initially, synthesis of 2benzoxazol2yl acetonitrile b was prepared by an equimolar mixture reactant 2amino phenol and malanonitrile. The compound 3 on diazotization reaction affords the tetrazole compound. Pdf synthesis of some novel benzoxazole derivatives and. The feiiisalen complex has been applied successfully as a catalyst for the novel, simple, efficient, and onepot multicomponent synthesis of benzoxazole derivatives from catechols, ammonium acetate as the nitrogen source, and aldehydes nontoxic and cheap alternatives of amines for the first time.
This method provides a novel route for the synthesis of benzimidazole and benzoxazole derivatives. The compound 3 on diazotization reaction affords the tetrazole. In this study, it is aimed to obtain new phortress analogues by bioisosteric replacement of benzothiazole core in the structure to benzoxazole ring system. Synthesis, characterization, and biological evaluation of. In addition, benzoxazole derivatives possess a variety of biological activities. Synthesis, characterization and biological evaluation of benzoxazole derivatives a p. The resultant was cooled and recrystallised from ethanol. In pursuit of designing novel chemical entities with antiprotozoal and antimicrobial activities, benzoxazolyl aniline was utilized as a privileged scaffold of a series of 3 benzoxazole 2yl phenylamine derivatives, 3benzoxazoloyl acetamide, and butyramide derivatives. Synthesis, molecular docking and antimicrobial evaluation of. Microwaveassisted synthesis of benzoxazoles derivatives. Synthesis and evaluation of anticancer benzoxazoles and. Synthesis and biological evaluation of novel 5,7dichloro.
School of chemistry, university of kwazulunatal, west ville campus, chilten hills, private bag 54001, durban4000, south africa. The method produced a wide variety of functionalized benzoxazole derivatives in good yields. Synthesis and anticholinesterase activities of novel glycosyl. Preliminary mechanistic experiments revealed that the reaction would procee synthetic methodology in obc. Here, an efficient and simple method for the synthesis of target compounds is described and the synthesis of some compounds has been reported in our previous studies. Synthesis and biological evaluation of novel 5,7dichloro1,3. As a result of the cyclization reaction, benzoxazole derivatives bearing an ester group. Widespread interest in the chemistry of benzoxazole derivatives in large number of products has attracted the researchers because of their. Facile and efficient synthesis of benzoxazole derivatives using novel.
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