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Journal articles on the topic 'Synthesis of benzoxazoles'

Author: Grafiati

Published: 4 June 2021

Last updated: 14 February 2022

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1

Özil, Musa, and Emre Menteşe. "Microwave-assisted Synthesis of Benzoxazoles Derivatives." Current Microwave Chemistry 7, no. 3 (December 30, 2020): 183–95. http://dx.doi.org/10.2174/2213335607999200518094114.

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Background: Benzoxazole, containing a 1,3-oxazole system fused with a benzene ring, has a profound effect on medicinal chemistry research owing to its important pharmacological activities. On the other hand, the benzoxazole derivative has exhibited important properties in material science. Especially in recent years, microwave-assisted synthesis is a technique that can be used to increase diversity and quick research in modern chemistry. The utilization of microwave irradiation is beneficial for the synthesis of benzoxazole in recent years. In this focused review, we provide a metaanalysis of studies on benzoxazole in different reaction conditions, catalysts, and starting materials by microwave technique so far, which is different from conventional heating. Methods: Synthesis of different kind of benzoxazole derivatives have been carried out by microwave irradiation. The most used method to obtain benzoxazoles is the condensation of 2-aminophenol or its derivatives with aldehydes, carboxylic acids, nitriles, isocyanates, and aliphatic amines. Results: Benzoxazole system and its derivatives have exhibited a broad range of pharmacological properties. Thus, many scientists have remarked on the importance of the synthesis of different benzoxazole derivatives. Conventional heating is a relatively inefficient and slow method to convey energy in orientation to the reaction medium. However, the microwave-assisted heating technique is a more effective interior heating by straight coupling of microwave energy with the molecules. Conclusion: In this review, different studies were presented on the recent details accessible in the microwave- assisted techniques on the synthesis of the benzoxazole ring. It presents all examples of such compounds that have been reported from 1996 to the present. Benzoxazoles showed an extensive class of chemical substances not only in pharmaceutical chemistry but also in dyestuff, polymer industries, agrochemical, and optical brighteners. Thus the development of fast and efficient achievement of benzoxazoles with a diversity of substituents in high yield is getting more noteworthy. As shown in this review, microwave-assisted synthesis of benzoxazoles is a very effective and useful technique.

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2

Kumar, Dinesh, Santosh Rudrawar, and Asit K. Chakraborti. "One-Pot Synthesis of 2-Substituted Benzoxazoles Directly from Carboxylic Acids." Australian Journal of Chemistry 61, no. 11 (2008): 881. http://dx.doi.org/10.1071/ch08193.

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Methanesulfonic acid has been found to be a highly effective catalyst for a convenient and one-pot synthesis of 2-substituted benzoxazoles by the reaction of 2-aminophenol with acid chlorides, generated in situ from carboxylic acids. Aryl, heteroaryl, and arylalkyl carboxylic acids provided excellent yields of the corresponding benzoxazoles. The reaction conditions were compatible with various substituents such as chloro, bromo, nitro, methoxy, cyclopentyloxy, phenoxy, thiophenoxy, and conjugated double bonds. Benzoxazole formation was found to be general with respect to substituted 2-aminophenols.

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3

Staniszewska, Monika, Łukasz Kuryk, Aleksander Gryciuk, Joanna Kawalec, Marta Rogalska, Joanna Baran, Edyta Łukowska-Chojnacka, and Anna Kowalkowska. "In Vitro Anti-Candida Activity and Action Mode of Benzoxazole Derivatives." Molecules 26, no. 16 (August 18, 2021): 5008. http://dx.doi.org/10.3390/molecules26165008.

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A newly synthetized series of N-phenacyl derivatives of 2-mercaptobenzoxazole, including analogues of 5-bromo- and 5,7-dibromobenzoxazole, were screened against Candida strains and the action mechanism was evaluated. 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(4-bromophenyl)ethanone (5d), 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(2,3,4-trichloro-phenyl)ethanone (5i), 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(2,4,6-trichlorophenyl)ethanone (5k) and 2-[(5-bromo-1,3-benzoxazol-2-yl)sulfanyl]-1-phenylethanone (6a) showed anti-C. albicans SC5314 activity, where 5d displayed MICT = 16 µg/mL (%R = 100) and a weak anti-proliferative activity against the clinical strains: C. albicans resistant to azoles (Itr and Flu) and C. glabrata. Derivatives 5k and 6a displayed MICP = 16 µg/mL and %R = 64.2 ± 10.6, %R = 88.0 ± 9.7, respectively, against the C. albicans isolate. Derivative 5i was the most active against C. glabrata (%R = 53.0 ± 3.5 at 16 µg/mL). Benzoxazoles displayed no MIC against C. glabrata. Benzoxazoles showed a pleiotropic action mode: (1) the total sterols content was perturbed; (2) 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(3,4-dichlorophenyl)ethanol and 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(2,3,4-trichlorophenyl)ethanol (8h–i) at the lowest fungistatic conc. inhibited the efflux of the Rho123 tracker during the membrane transport process; (3) mitochondrial respiration was affected/inhibited by the benzoxazoles: 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(4-chlorophenyl)ethanol and 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(4-bromophenyl)ethanol 8c–d and 8i. Benzoxazoles showed comparable activity to commercially available azoles due to (1) the interaction with exogenous ergosterol, (2) endogenous ergosterol synthesis blocking as well as (3) membrane permeabilizing properties typical of AmB. Benzoxazoles display a broad spectrum of anti-Candida activity and action mode towards the membrane without cross-resistance with AmB; furthermore, they are safe to mammals.

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4

Arisoy, Mustafa, Ozlem Temiz-Arpaci, Fatma Kaynak-Onurdag, and Selda Ozgen. "Synthesis and Antimicrobial Evaluation of 2-(p-Substituted Phenyl)-5-[(4-substituted piperazin-1-yl)acetamido]-benzoxazoles." Zeitschrift für Naturforschung C 69, no. 9-10 (October 1, 2014): 368–74. http://dx.doi.org/10.5560/znc.2014-0024.

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Abstract series of 2-(p-substituted phenyl)-5-(2-{4-[(p-chloro-fluorophenyl)=phenyl] piperazin-1-yl}- acetamido)-benzoxazoles were synthesized and tested for their antimicrobial activities. The structures of the new derivatives were elucidated by spectral techniques. The minimum inhibitory concentrations (MIC) of the new benzoxazoles, along with those of previously synthesized analogues, were determined against standard bacterial and fungal strains and drug-resistant isolates, and compared with those of several reference drugs. The new benzoxazole derivatives were found to possess a broad spectrum of antimicrobial activity with MIC values of 32 - 1024 μg/ml. Although the standard drugs were more active against the tested pathogens, the activities of the new benzoxazoles and the reference drugs were largely similar against the drug-resistant isolates.

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5

Glamočlija, Una, Subhash Padhye, Selma Špirtović-Halilović, Amar Osmanović, Elma Veljović, Sunčica Roca, Irena Novaković, et al. "Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone." Molecules 23, no. 12 (December 12, 2018): 3297. http://dx.doi.org/10.3390/molecules23123297.

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Thymoquinone (TQ), a natural compound with antimicrobial and antitumor activity, was used as the starting molecule for the preparation of 3-aminothymoquinone (ATQ) from which ten novel benzoxazole derivatives were prepared and characterized by elemental analysis, IR spectroscopy, mass spectrometry and NMR (1H, 13C) spectroscopy in solution. The crystal structure of 4-methyl-2-phenyl-7-isopropyl-1,3-benzoxazole-5-ol (1a) has been determined by X-ray diffraction. All compounds were tested for their antibacterial, antifungal and antitumor activities. TQ and ATQ showed better antibacterial activity against tested Gram-positive and Gram-negative bacterial strains than benzoxazoles. ATQ had the most potent antifungal effect against Candida albicans, Saccharomyces cerevisiae and Aspergillus brasiliensis. Three benzoxazole derivatives and ATQ showed the highest antitumor activities. The most potent was 2-(4-fluorophenyl)-4-methyl-7-isopropyl-1,3-benzoxazole-5-ol (1f). Western blot analyses have shown that this compound inhibited phosphorylation of protein kinase B (Akt) and Insulin-like Growth Factor-1 Receptor (IGF1R β) in HeLa and HepG2 cells. The least toxic compound against normal fibroblast cells, which maintains similar antitumor activities as TQ, was 2-(4-chlorophenyl)-4-methyl-7-isopropyl-1,3-benzoxazole-5-ol (1e). Docking studies indicated that 1e and 1f have significant effects against selected receptors playing important roles in tumour survival.

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6

Aruna, G., Ravindra Kulkarni, Baswaraj Machaa, Malathi Jojula, Shravan Gunda, and G. Achaiah. "Design, Synthesis and Evaluation of Aryloxybenzylidene Hydrazinyl-Benzoxazoles/Benzothiazoles Analogs as Antimycobacterial Agents." Asian Journal of Organic & Medicinal Chemistry 5, no. 3 (2020): 185–91. http://dx.doi.org/10.14233/ajomc.2020.ajomc-p272.

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Substituted 2-(2-(4-aryloxybenzylidene)hydrazinyl)benzothiazole/benzoxazoles series were designed through molecular hybridization and synthesized in condensation reaction of hydrazinylbenzothiazole/ benzoxazole with substituted aryloxy benzaldehydes. All the synthesized compounds were assigned structure based on spectral data and were evaluated for antimycobacterial activity. Among both benzothiazole and benzoxazole derivatives, the compounds 8f and 9e were found to show most potent antitubercular activity with MIC value of 0.89 and 0.92 μM which are on a par with those of standard antitubercular drugs. In order to know the binding interactions of all the compounds were docked within the mycobacterial pantothenate synthetase, which showed interactions with Asp88, Arg200, Ser196, Asn199, Met 195 and Lys 160 of pantothenate synthetase.

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7

Imramovsky, Ales, Jan Kozic, Matus Pesko, Jirina Stolarikova, Jarmila Vinsova, Katarina Kralova, and Josef Jampilek. "Synthesis and Antimycobacterial and Photosynthesis-Inhibiting Evaluation of 2-[(E)-2-Substituted-ethenyl]-1,3-benzoxazoles." Scientific World Journal 2014 (2014): 1–11. http://dx.doi.org/10.1155/2014/705973.

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A series of twelve 2-[(E)-2-substituted-ethenyl]-1,3-benzoxazoles was designed. All the synthesized compounds were tested against three mycobacterial strains. The compounds were also evaluated for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleraceaL.) chloroplasts. 2-[(E)-2-(4-Methoxyphenyl)ethenyl]-1,3-benzoxazole, 2-[(E)-2-(2,3-dihydro-1-benzofuran-5-yl)ethenyl]-1,3-benzoxazole and 2-{(E)-2-[4-(methylsulfanyl)phenyl]ethenyl}-1,3-benzoxazole showed the highest activity againstM. tuberculosis,M. kansasii,andM. avium, and they demonstrated significantly higher activity againstM. aviumandM. kansasiithan isoniazid. The PET-inhibiting activity of the most activeortho-substituted compound 2-[(E)-2-(2-methoxyphenyl)ethenyl]-1,3-benzoxazole was IC50= 76.3 μmol/L, while the PET-inhibiting activity ofpara-substituted compounds was significantly lower. The site of inhibitory action of tested compounds is situated on the donor side of photosystem II. The structure-activity relationships are discussed.

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8

Malakar, Chandi, Nagaraju Vodnala, Raghuram Gujjarappa, Arup Kabi, Mohan Kumar, and Uwe Beifuss. "Facile Protocols towards C2-Arylated Benzoxazoles using Fe(III)-Catalyzed C(sp 2-H) Functionalization and Metal-Free Domino Approach." Synlett 29, no. 11 (May 16, 2018): 1469–78. http://dx.doi.org/10.1055/s-0037-1609718.

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Considering their growing attention in the field of medicinal chemistry and drug-discovery research, the facile and convenient approaches towards the preparation of 2-aryl benzoxazole derivatives have been described. The transformation is accomplished by using Fe(III)-catalyzed C–H activation of benzoxazoles with boronic acids to obtain a wide range of C2-arylated benzoxazoles in high yields. The developed method excludes the formation of self-coupling compounds as side products. On the other hand, the synthesis of the products is also achieved via a metal-free domino protocol by the reaction between 1-nitroso-2-naphthol and acetophenones using catalytic amounts of CBr4 in the presence of Cs2CO3 as base. The devised tandem method avoids the use of pre-activated α-haloketones as substrates. Due to their immense impact in marketed drugs and molecules under clinical trial, the described method can be a powerful tool for their synthesis which restricts the use of precious metals as catalyst.

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9

M, Jyothi, and Ramchander Merugu. "AN UPDATE ON THE SYNTHESIS OF BENZOXAZOLES." Asian Journal of Pharmaceutical and Clinical Research 10, no. 10 (September 1, 2017): 48. http://dx.doi.org/10.22159/ajpcr.2017.v10i10.19457.

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Benzoxazoles being structurally similar to bases adenine and guanine interact with biomolecules present in living systems. These compounds possess antimicrobial, central nervous system activities, antihyperglycemic potentiating activity, analgesic, and anti-inflammatory activity. It can also be used as starting material for other bioactive molecules. Modifications in structure and the biological profiles of new generations of benzoxazoles were found to be more potent with enhanced biological activity. Considering all these, we have prepared this review and discussed the synthesis and biological activities of benzoxazoles.

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10

Kale, Dolly, Gajanan Rashinkar, Audumbar Patil, Arjun Kumbhar, and Rajashri Salunkhe. "Facile Access to 2-Substituted Benzoxazoles Using Sawdust Supported N-Heterocyclic Carbene-Ni Complex via C-H Activation." Letters in Organic Chemistry 17, no. 6 (May 20, 2020): 479–89. http://dx.doi.org/10.2174/1570178616666190705153927.

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Sawdust supported N-heterocyclic carbene-nickel complex has been prepared by covalent grafting of 1-methyl imidazole in the matrix of chloropropyl modified sawdust followed by reaction with nickel acetate. The resultant NHC-Ni complex was employed as a heterogeneous catalyst for the synthesis of 2-substituted benzoxazoles from benzoxazole and aryl boronic acids following C-H activation strategy. The recycling experiments showed that the complex could be reused for five consecutive runs without significant loss in the yield of products.

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11

Arisoy, Mustafa, Ozlem Temiz-Arpaci, Fatma Kaynak-Onurdag, and Selda Ozgen. "Synthesis and Antimicrobial Activity of Novel Benzoxazoles." Zeitschrift für Naturforschung C 67, no. 9-10 (October 1, 2012): 466–72. http://dx.doi.org/10.1515/znc-2012-9-1004.

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A series of 2-(p-substituted-benzyl)-5-[[4-(p-chloro/fluoro-phenyl)piperazin-1-yl]ace tamido] -benzoxazoles were synthesized in need of new compounds for the fight against microbial pathogens. Their structures were elucidated by spectral techniques. These new derivatives, along with previously synthesized 2-(p-substituted-benzyl)-5-substituted-benzoxazoles, were evaluated for their antibacterial and antifungal activities against standard strains and drugresistant isolates in comparison with ampicillin, gentamicin sulfate, ofloxacin, vancomycin, fluconazole, and amphotericin B trihydrate. The minimum inhibitory concentration (MIC) of each compound was determined by a two-fold serial dilution technique. The compounds were found to possess a broad spectrum of antimicrobial activities with MIC values of 32 - 256 μg/ml. Although standard drugs were more active against the pathogenes employed in this study, the activities of the new benzoxazoles and reference drugs against drug-resistant isolates of the microorganisms were largely similar

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12

Garrido, Amanda, Pierre-Olivier Delaye, François Quintin, Mohamed Abarbri, Pedro Lameiras, Alain Gueiffier, Jérôme Thibonnet, and Julien Petrignet. "Direct Access to Highly Functionalised Benzimidazoles and Benzoxazoles from a Common Precursor." Synthesis 51, no. 21 (August 6, 2019): 4006–13. http://dx.doi.org/10.1055/s-0039-1690153.

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Benzoxazole and benzimidazole are commonly encountered heterocycles in medicinal chemistry and their functionalisation around 1-, 2-, 5-, and/or 6-positions provides a wide range of molecules of biological interest. In this manuscript, a straightforward preparation of diversely and highly substituted benzimidazoles and benzoxazoles on these positions, from a common starting material, a 3,3-dibromoacrolein, is described. Such acrolein derivatives are almost never described in the literature or used as ‘building-block’ for organic synthesis. The double electrophilicity of this substrate was found to be advantageous for condensation with two equivalents of various 1,2-diaminobenzene or 2-aminophenol derivatives. This one-pot reaction performed under metal-free and mild conditions allows the creation of three new carbon–heteroatom bonds and affords the desired heterocycles.

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13

Gieshoff, Tile, Anton Kehl, Dieter Schollmeyer, Kevin D. Moeller, and Siegfried R. Waldvogel. "Electrochemical synthesis of benzoxazoles from anilides – a new approach to employ amidyl radical intermediates." Chemical Communications 53, no. 20 (2017): 2974–77. http://dx.doi.org/10.1039/c7cc00927e.

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14

Tian, Qingqiang, Wen Luo, Zongjie Gan, Dan Li, Zeshu Dai, Huajun Wang, Xuetong Wang, and Jianyong Yuan. "Eco-Friendly Syntheses of 2-Substituted Benzoxazoles and 2-Substituted Benzothiazoles from 2-Aminophenols, 2-Aminothiophenols and DMF Derivatives in the Presence of Imidazolium Chloride." Molecules 24, no. 1 (January 4, 2019): 174. http://dx.doi.org/10.3390/molecules24010174.

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A simple, economical and metal-free approach to the synthesis of 2-substituted benzoxazoles and 2-substituted benzothiazoles from 2-aminophenols, 2-aminothiophenols and DMF derivatives, only using imidazolium chloride (50% mmol) as promoter without any other additive, was reported. Various 2-substituted benzoxazoles and 2-substituted benzothiazoles were thus prepared in moderate to excellent yields.

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15

Tang, Yanling, Minxin Li, Hui Gao, Gaoxiong Rao, and Zewei Mao. "Efficient Cu-catalyzed intramolecular O-arylation for synthesis of benzoxazoles in water." RSC Advances 10, no. 24 (2020): 14317–21. http://dx.doi.org/10.1039/d0ra00570c.

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16

Yang, Bo, Weiye Hu, and Songlin Zhang. "Synthesis of benzoxazoles via an iron-catalyzed domino C–N/C–O cross-coupling reaction." RSC Advances 8, no. 5 (2018): 2267–70. http://dx.doi.org/10.1039/c7ra13080e.

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17

Safaei, Elham, Zahra Alaji, Farhad Panahi, Andrzej Wojtczak, and Janez Zvonko Jagličić. "Synthesis and characterization of a novel oxo-bridged binuclear iron(iii) complex: its catalytic application in the synthesis of benzoxazoles using benzyl alcohol in water." New Journal of Chemistry 42, no. 9 (2018): 7230–36. http://dx.doi.org/10.1039/c8nj00921j.

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18

Gao, Sen, Liming Gao, Hong Meng, Meiming Luo, and Xiaoming Zeng. "Iron-catalyzed synthesis of benzoxazoles by oxidative coupling/cyclization of phenol derivatives with benzoyl aldehyde oximes." Chemical Communications 53, no. 71 (2017): 9886–89. http://dx.doi.org/10.1039/c7cc04965j.

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19

Wu, Fengtian, Jie Zhang, Qianbing Wei, Ping Liu, Jianwei Xie, Haojie Jiang, and Bin Dai. "Copper-catalysed intramolecular O-arylation: a simple and efficient method for benzoxazole synthesis." Org. Biomol. Chem. 12, no. 47 (2014): 9696–701. http://dx.doi.org/10.1039/c4ob02068e.

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20

Urzúa, Julio I., Renato Contreras, Cristian O. Salas, and Ricardo A. Tapia. "N-Heterocyclic carbene copper(i) complex-catalyzed synthesis of 2-aryl benzoxazoles and benzothiazoles." RSC Advances 6, no. 85 (2016): 82401–8. http://dx.doi.org/10.1039/c6ra18510j.

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21

Arisoy, Mustafa, Ozlem Temiz-Arpaci, Fatma Kaynak-Onurdag, and Selda Ozgen. "Synthesis and Antimicrobial Activity of Novel Benzoxazoles." Zeitschrift für Naturforschung C 67 (2012): 0466. http://dx.doi.org/10.5560/znc.2012.67c0466.

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22

Wang, Kaixuan, and Lanzhi Wang. "Unexpected Rearrangement Reaction and Synthesis of Benzoxazoles." Chinese Journal of Organic Chemistry 39, no. 4 (2019): 1147. http://dx.doi.org/10.6023/cjoc201809038.

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23

Spatz, Julia H., Thorsten Bach, Michael Umkehrer, Julien Bardin, Günther Ross, Christoph Burdack, and Jürgen Kolb. "Diversity oriented synthesis of benzoxazoles and benzothiazoles." Tetrahedron Letters 48, no. 51 (December 2007): 9030–34. http://dx.doi.org/10.1016/j.tetlet.2007.10.067.

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24

Tao, Kemei, Jianlong Zheng, Zhaogui Liu, Wang Shen, and Jiancun Zhang. "Facile synthesis of benzoxazoles from 1,1-dibromoethenes." Tetrahedron Letters 51, no. 24 (June 2010): 3246–49. http://dx.doi.org/10.1016/j.tetlet.2010.04.071.

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25

Kiran, Kuppalli R., Toreshettahally R. Swaroop, Kodipura P. Sukrutha, Jeegundipattana B. Shruthi, Seegehally M. Anil, Kanchugarakoppal S. Rangappa, and Maralinganadoddi P. Sadashiva. "Acid-Catalyzed Condensation of o-Phenylenediammines and o-Aminophenols with α-Oxodithioesters: A Divergent and Regioselective Synthesis of 2-Methylthio-3-aryl/Heteroarylquinoxalines and 2-Acylbenzoxazoles." Synthesis 51, no. 22 (September 23, 2019): 4205–14. http://dx.doi.org/10.1055/s-0039-1690616.

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o-Phenylenediammines and o-aminophenols were reacted with α-oxodithioesters in a highly regioselective fashion to give 2-methylthio-3-aryl/heteroarylquinoxalines and 2-acylbenzoxazoles in 55–94% and 45–86%, respectively, in the presence of p-toluene sulfonic acid catalyst. Control experiments involving reaction of aniline with a α-oxodithioester indicated that the thiocarbonyl group is more reactive than the carbonyl group. Based on this, probable mechanisms for the formation of quinoxalines and benzoxazoles are given. Biological targets of the quinoxalines and benzoxazoles were identified by bioinformatics. It was found that quinoxalines have good binding affinity with human dual-specificity tyrosine-phosphorylation-regulated kinase 1A and benzoxazoles with human carboxylesterase.

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Hajipour, Abdol R., Zahra Khorsandi, Maryam Mortazavi, and Hossein Farrokhpour. "Green, efficient and large-scale synthesis of benzimidazoles, benzoxazoles and benzothiazoles derivatives using ligand-free cobalt-nanoparticles: as potential anti-estrogen breast cancer agents, and study of their interactions with estrogen receptor by molecular docking." RSC Advances 5, no. 130 (2015): 107822–28. http://dx.doi.org/10.1039/c5ra22207a.

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27

Chen, Lijun, Lin Ju, Katelyn A. Bustin, and Jessica M. Hoover. "Copper-catalyzed oxidative decarboxylative C–H arylation of benzoxazoles with 2-nitrobenzoic acids." Chemical Communications 51, no. 81 (2015): 15059–62. http://dx.doi.org/10.1039/c5cc06645j.

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Nguyen, Oanh T. K., Long T. Nguyen, Nhu K. Truong, Viet D. Nguyen, Anh T. Nguyen, Nhan T. H. Le, Dung T. Le, and Nam T. S. Phan. "Synthesis of triphenylamines via ligand-free selective ring-opening of benzoxazoles or benzothiazoles under superparamagnetic nanoparticle catalysis." RSC Advances 7, no. 65 (2017): 40929–39. http://dx.doi.org/10.1039/c7ra06168d.

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Tiwari, Abhishek R., and Bhalchandra M. Bhanage. "Copper-catalyzed synthesis of benzoxazoles via tandem cyclization of 2-halophenols with amidines." Organic & Biomolecular Chemistry 14, no. 33 (2016): 7920–26. http://dx.doi.org/10.1039/c6ob01264g.

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Carvalho, Larissa Incerti Santos de, Dalila Junqueira Alvarenga, Letícia Cruz Ferreira do Carmo, Lucas Gomes de Oliveira, Naiara Chaves Silva, Amanda Latércia Tranches Dias, Luiz Felipe Leomil Coelho, Thiago Belarmino de Souza, Danielle Ferreira Dias, and Diogo Teixeira Carvalho. "Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp." Journal of Chemistry 2017 (2017): 1–8. http://dx.doi.org/10.1155/2017/5207439.

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Eugenol is a natural allylphenol responsible for a wide range of biological activities, especially antimicrobial. Benzoxazoles are heterocycles with recognized antimicrobial activities. This paper describes the design, synthesis, and the biological results for benzoxazole type derivatives of eugenol as antifungal agents. The products were obtained in good yields by a four-step synthetic sequence involving aromatic nitration, nitroreduction, amide formation, and cycle condensation. They were evaluated against species of Candida spp. in microdilution assays, and four products (5a, 5b′, 5c, and 5d′) were about five times more active than eugenol against C. albicans and C. glabrata. Two of them (5b′ and 5d′) showed good activity against C. krusei, a species which is naturally resistant to fluconazole. Furthermore, the active products were more selective than eugenol against human blood cells, showing that they are interesting substances for further optimization.

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Angeli, A., T. S. Peat, G. Bartolucci, A. Nocentini, C. T. Supuran, and F. Carta. "Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors." Organic & Biomolecular Chemistry 14, no. 48 (2016): 11353–56. http://dx.doi.org/10.1039/c6ob02299e.

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32

Yang, Daoshan, Xiao Zhu, Wei Wei, Nana Sun, Li Yuan, Min Jiang, Jinmao You, and Hua Wang. "Magnetically recoverable and reusable CuFe2O4 nanoparticle-catalyzed synthesis of benzoxazoles, benzothiazoles and benzimidazoles using dioxygen as oxidant." RSC Adv. 4, no. 34 (2014): 17832–39. http://dx.doi.org/10.1039/c4ra00559g.

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A green and efficient strategy for the synthesis of benzoxazoles, benzothiazoles and benzimidazoles has been developed by using inexpensive, readily available, dioxygen-stable and recyclable CuFe₂O₄ as the nanocatalyst.

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Temiz-Arpaci, O., B. Eylem Cifcioglu Goztepe, Fatma Kaynak-Onurdag, Selda Ozgen, Fatma Senol, and I. Erdogan Orhan. "Synthesis and different biological activities of novel benzoxazoles." Acta Biologica Hungarica 64, no. 2 (June 2013): 249–61. http://dx.doi.org/10.1556/abiol.64.2013.2.10.

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34

Beebe, Xenia, Dariusz Wodka, and Thomas J. Sowin. "Solid-Phase Synthesis of Benzoxazoles from 3-Nitrotyrosine." Journal of Combinatorial Chemistry 3, no. 4 (July 2001): 360–66. http://dx.doi.org/10.1021/cc010002v.

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35

Wang, Fengjiang, and James R. Hauske. "Solid-phase synthesis of benzoxazoles via mitsunobu reaction." Tetrahedron Letters 38, no. 37 (September 1997): 6529–32. http://dx.doi.org/10.1016/s0040-4039(97)01527-x.

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36

Jadhav, R. K., A. B. Nikumbh, and B. K. Karale. "Synthesis and Screening of Fluoro Substituted Pyrazolyl Benzoxazoles." Oriental Journal of Chemistry 31, no. 2 (June 20, 2015): 967–72. http://dx.doi.org/10.13005/ojc/310242.

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37

Koleda, Olesja, Timo Broese, Jan Noetzel, Michael Roemelt, Edgars Suna, and Robert Francke. "Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine." Journal of Organic Chemistry 82, no. 22 (August 25, 2017): 11669–81. http://dx.doi.org/10.1021/acs.joc.7b01686.

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Matsuo, Shigeru, and Ken-ichi Mitsuhashi. "Synthesis and properties of poly(arylene ether benzoxazoles)." Journal of Polymer Science Part A: Polymer Chemistry 32, no. 11 (August 1994): 2199–201. http://dx.doi.org/10.1002/pola.1994.080321124.

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39

Olagbemiro, T. O., M. O. Agho, O. J. Abayeh, and J. O. Amupitan. "Facile synthesis of 2-substituted benzoxazoles via ketenes." Recueil des Travaux Chimiques des Pays-Bas 115, no. 6 (September 2, 2010): 337–38. http://dx.doi.org/10.1002/recl.19961150606.

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40

Temiz-Arpacı, Özlem, İlkay Yıldız, Semiha Özkan, Fatma Kaynak, Esin Akı-Şener, and İsmail Yalçın. "Synthesis and biological activity of some new benzoxazoles." European Journal of Medicinal Chemistry 43, no. 7 (July 2008): 1423–31. http://dx.doi.org/10.1016/j.ejmech.2007.09.023.

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41

El-Shafei, Ahmed K., Ahmed M. M. El-Saghier, and Ahmed M. Soliman. "Synthesis of Heterocyclic Ketene N,S-Acetals and Their Reactions with α,β-Unsaturated Nitriles." Collection of Czechoslovak Chemical Communications 60, no. 6 (1995): 1065–69. http://dx.doi.org/10.1135/cccc19951065.

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Abstract:

Substituted 3H-pyrido[2,1-b]benzoxazoles and 3H-pyrido[2,1-b]benzothiazoles were prepared by base catalyzed cycloaddition of benzylidenemalonitrile with benzoxazolylidene- or benzothiazolylidenepentane-1,3-dione.

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42

Rao, Mugada Sugunakara, and Sahid Hussain. "TEMPO-mediated aerobic oxidative synthesis of 2-aryl benzoxazoles via ring-opening of benzoxazoles with benzylamines." Synthetic Communications 51, no. 17 (July 14, 2021): 2684–94. http://dx.doi.org/10.1080/00397911.2021.1949476.

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43

Aksenov, Nicolai A., Alexander V. Aksenov, Oleg N. Nadein, Dmitrii A. Aksenov, Alexander N. Smirnov, and Michael Rubin. "One-pot synthesis of benzoxazoles via the metal-free ortho-C–H functionalization of phenols with nitroalkanes." RSC Advances 5, no. 88 (2015): 71620–26. http://dx.doi.org/10.1039/c5ra15128g.

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Abstract:

PPA-activated nitroalkanes are employed in the design of a one-pot cascade transformation involvingortho-C–H functionalization, by Beckman rearrangement, and condensation to produce benzoxazoles and benzobisoxazoles directly from phenols.

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44

Nishioka, Hiromi, Takashi Harayama, Yukiko Ohmori, Yumiko Iba, and Eri Tsuda. "Novel Synthesis of Benzoxazoles from o-Nitrophenols and Amines." HETEROCYCLES 64, no. 1 (2004): 193. http://dx.doi.org/10.3987/com-04-s(p)11.

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Xiao, Liwei, Hongjie Gao, Jie Kong, Guangxian Liu, Xiaoxia Peng, and Shujun Wang. "Progress in the Synthesis of 2-Substituted Benzoxazoles Derivatives." Chinese Journal of Organic Chemistry 34, no. 6 (2014): 1048. http://dx.doi.org/10.6023/cjoc201401030.

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46

Pottorf, Richard S., Naresh K. Chadha, Martins Katkevics, Vita Ozola, Edgars Suna, Hadi Ghane, Tor Regberg, and Mark R. Player. "Parallel synthesis of benzoxazoles via microwave-assisted dielectric heating." Tetrahedron Letters 44, no. 1 (January 2003): 175–78. http://dx.doi.org/10.1016/s0040-4039(02)02495-4.

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Temiz-Arpaci, Ozlem, Fatma Doğanc, Duygu Sac, Elmas Sari, Fatma Kaynak-Onurdag, and Suzan Okten. "Synthesis and antimicrobial evaluation of some novel sulfonylamido-benzoxazoles." Acta Biologica Hungarica 67, no. 1 (March 2016): 75–84. http://dx.doi.org/10.1556/018.67.2016.1.6.

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48

Nieddu, Giammario, and Giampaolo Giacomelli. "A microwave assisted synthesis of benzoxazoles from carboxylic acids." Tetrahedron 69, no. 2 (January 2013): 791–95. http://dx.doi.org/10.1016/j.tet.2012.10.084.

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Akolkar, H. N., and B. K. Karale. "Synthesis and Characterization of Novel Thiazole Anchored Pyrazolyl Benzoxazoles." Oriental Journal of Chemistry 31, no. 1 (March 28, 2015): 431–33. http://dx.doi.org/10.13005/ojc/310151.

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50

Cho, Chan Sik, Dong Tak Kim, Jiao Qiang Zhang, Son-Lam Ho, Tae-Jeong Kim, and Sang Chul Shim. "Tin(II) chloride-mediated synthesis of 2-substituted benzoxazoles." Journal of Heterocyclic Chemistry 39, no. 2 (March 2002): 421–23. http://dx.doi.org/10.1002/jhet.5570390229.

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