840-37-9Relevant academic research and scientific papers
Heterogeneous palladium (II)-complexed dendronized polymer: A rare palladium catalyst for the one-pot synthesis of 2-arylbenzoxazoles
George, Smitha,Sreekumar, Krishnapillai
, (2020/12/14)
The palladium complex of dendronized amine polymer (EG–Gn–Pd, n = 0, 1 and 2) having ethylene glycol-initiated polyepichlorohydrin as core was synthesized on a Merrifield resin support and was well characterized. Generally, palladium catalysts are known for carbon–carbon coupling reactions. Here, a developed catalyst was found to be good for benzoxazole synthesis. Higher generation dendronized polymer (EG–G2–Pd) was found to be better catalyst over lower generation dendronized polymers. Moreover, dendronized polymers were found to be a better catalyst over dendrigraft polymers. The catalyst reusability was checked and good yield was obtained for five cycles.
Fluorinated phosphoric acid as a versatile effective catalyst for synthesis of series of benzimidazoles, benzoxazoles and benzothiazoles at room temperature
Mathapati, Sushil R.,Patil, Komal N.,Mathakari, Sujit S.,Suryawanshi, Appasaheb W.,Jadhav, Arvind H.
, p. 538 - 547 (2021/01/21)
The present work describes synthesis of a series of benzimidazoles, benzoxazoles and benzothiazoles through the cyclization of 1, 2-phenylenediamine, 2-aminothiophenol, or 2-aminophenol with aryl, aliphatic and heteroaryl aldehydes. The present synthetic protocol is very much efficient in presence of 5 mol % fluorophosphoric acid as a catalyst in ethanol solvent at room temperature. Shorter reaction time, simple work-up technique, high yields and easy availability are specific compensations of the present synthetic approach.
In-vitro Anti-cancer assay and apoptotic cell pathway of newly synthesized benzoxazole-N-heterocyclic hybrids as potent tyrosine kinase inhibitors
Desai, Sulaksha,Desai, Vidya,Shingade, Sunil
supporting information, (2019/11/13)
A series of benzoxazole-N-heterocyclic hybrids have been synthesized by a one-pot strategy. Molecular docking study revealed that such compounds have the ability to inhibit enzyme protein tyrosine kinase. The findings of this work have been the successful synthesis of benzoxazole scaffolds, featuring hybrids of benzoxazole with quinoline and quinoxaline respectively. The molecular docking studies have showed these compounds to be inhibitors of tyrosine kinase enzyme which triggers growth of cancer cells. The cytotoxicity study of compounds 4a-f showed better potency against breast cancer cell lines MCF-7 and MDA-MB-231 in contrast to oral and lung cancer cell lines KB and A549. The tyrosine kinase activity was measured using Universal Tyrosine Kinase Assay kit using horseradish peroxide (HRP)-conjugated anti-phosphotyrosine kinase solution as a substrate. The compounds 4c exhibited maximum inhibition in the activity of enzyme tyrosine kinase with IC50 value 0.10 ± 0.16 μM, than other compounds which were studied and thus proved to be inhibitors of enzyme tyrosine kinase. The selective index of all four compounds was found out to be greater than two, indicating the non-toxic behaviour, i.e. good anti-cancer activity. Further, fluorescence microscopic study helped to characterize the mode of cell death, which was found to be late apoptosis as indicated by the orange fluorescence. The SAR analysis has also been carried out.
Method for synthesizing benzoxazole through microwave radiation of benzamide compound in water phase
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Paragraph 0042, (2019/03/08)
The invention discloses a method for synthesizing benzoxazole through microwave radiation of a benzamide compound in a water phase. The benzamide compound is added into the water phase under the microwave condition to be subjected to a cyclization reaction for generating the benzoxazole under the alkali condition, and the method for preparing the benzoxazole is environmentally friendly, easy and convenient to operate, safe, low in cost and efficient. Compared with the prior art, the method can be applied to a large number of functional groups, the yield is high, the number of by-products is small, and the method is easy to operate, safe, low in cost and environmentally friendly. (Please see the specifications for the formula).
A Predictive Model for the Decarboxylation of Silver Benzoate Complexes Relevant to Decarboxylative Coupling Reactions
Crovak, Robert A.,Hoover, Jessica M.
supporting information, p. 2434 - 2437 (2018/02/28)
Decarboxylative coupling reactions offer an attractive route to generate functionalized arenes from simple and readily available carboxylic acid coupling partners, yet they are underutilized due to limitations in the scope of carboxylic acid coupling partner. Here we report that the field effect parameter (F) has a substantial influence on the rate of decarboxylation of well-defined silver benzoate complexes. This finding provides the opportunity to surpass current substrate limitations associated with decarboxylation and to enable widespread utilization of decarboxylative coupling reactions.
Anti-bacterial, catalytic and docking behaviours of novel di/trimeric imidazolium salts
Ganapathi, Pandurangan,Ganesan, Kilivelu
, p. 452 - 464 (2017/03/24)
Flexible di/trimeric substituted imidazolium salts are prepared under conventional/solvent free silica supported approaches. Solid supported approaches are superior than the conventional method like environment friendly, higher yield, shorter reaction time and easy workup procedure. We have studied the catalytic activities of our synthesized di/trimeric imidazolium salts for one-pot preparation of benzoxazole derivatives under conventional/Muffle furnace conditions. We have monitored the efficiency of recycled flexible di/trimeric imidazolium salts up to fourth cycles showed excellent responses. We have studied the MIC and MBC of our di/trimeric imidazolium salts against Gram positive/negative microorganisms under micro dilution method. Nitro substituted imidazolium salts showed excellent screening responses than the unsubstituted compounds. Computer assisted docking analysis is carried out for all our synthesized compounds. The host-guest interaction via hydrogen bonding between standard and our drug molecules against various human Gram positive and negative pathogens are compared. From the docking analysis, our drug molecules showed effective interaction against test pathogens.
Catalyst-free microwave-promoted one pot synthesis of 2-aryl benzoxazoles using MnO2 nanoparticles as a convenient oxidant under mild condition
Naeimi, Hossein,Rouzegar, Zahra,Rahmatinejad, Soraya
, p. 4745 - 4758 (2017/07/22)
Abstract: An efficient and facile protocol for one pot synthesis of a series of 2-aryl benzoxazoles through coupling of o-aminophenol with aromatic aldehydes under microwave irradiation in the presence of MnO2 nanoparticles as oxidant reagent was demonstrated. The MnO2 nanoparticles were prepared via a solid-state chemical reaction technique. The structure of oxidant was assigned by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), and scanning electron microscopy (SEM). The target molecules were obtained in good to high yields, high purity and short reaction times. The pure products were identified and characterized by physical and spectral data such as; melting point, IR, 1H NMR and 13C NMR. Graphical Abstract: An efficient and facil protocol for one pot synthesis of a series of 2-aryl benzoxazoles through coupling of o-aminophenol with aromatic aldehydes under microwave irradiation in the precense of MnO2 nanoparticles as oxidant reagent was demonstrated.
Sonocatalyzed facile synthesis of 2-aryl benzoxazoles using MnO2 nanoparticles as oxidant agent under mild conditions
Naeimi, Hossein,Rouzegar, Zahra,Rahmatinejad, Soraya
supporting information, p. 2087 - 2095 (2017/10/26)
Nano MnO2 was found to be an efficient oxidant agent for the synthesis of 2-substituted benzoxazoles through one-pot reaction of o-aminophenol and different aromatic aldehydes in acetonitrile under ultrasonic irradiation. This method was performed under mild conditions with high yields, inexpensive and readily available oxidant agent, facile and easy experimental procedure, simple purification of final products, and short reaction times. The prepared nano MnO2 has been characterized by FTIR, XRD, and SEM techniques. The pure products were identified and characterized by physical and spectroscopic data such as; melting point, IR, 1H NMR, and 13C NMR.
Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine
Koleda, Olesja,Broese, Timo,Noetzel, Jan,Roemelt, Michael,Suna, Edgars,Francke, Robert
, p. 11669 - 11681 (2017/11/24)
The indirect ("ex-cell") electrochemical synthesis of benzoxazoles from imines using a redox mediator based on the iodine(I)/iodine(III) redox couple is reported. Tethering the redox-active iodophenyl subunit to a tetra-alkylammonium moiety allowed for anodic oxidation to be performed without supporting electrolyte. The mediator salt can be easily recovered and reused. Our "ex-cell" approach toward the electrosynthesis of benzoxazoles is compatible with a range of redox-sensitive functional groups. An unprecedented concerted reductive elimination mechanism for benzoxazole formation is proposed on the basis of control experiments and DFT calculations.
Copper-Catalyzed Chelation-Assisted ortho-Nitration of 2-Aryls Using Pharmacophoric Benzothiazoles and Benzoxazoles as Directing Groups
Vinayak, Botla,Ashok, Akudari,Chandrasekharam, Malapaka
, p. 7127 - 7132 (2017/12/28)
A copper-catalyzed chelation-assisted ortho-nitration reaction of aryl derivtives has been achieved, using benzazoles as efficient directing groups. The reaction is general and efficient for aryl derivatives with various electronic properties, and also with different pharmacophorically important directing groups, i.e., benzoxazoles, benzothiazoles, and benzimidazoles. The nitro-group-containing products have significance as fluorogenic compounds and potential nitroreductase substrates that could be used for the detection of clinically important microorganisms. The nitration reaction proceeds with an inexpensive copper catalyst and a mild, cheap, and environmentally friendly nitro source, Fe(NO3)3·9H2O. This operationally simple and functional-group-tolerant protocol for the nitration of 2-aryl benzazoles proceeds with a high regioselectivity without the exclusion of air or moisture.
