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Journal articles on the topic 'Benzoxazole – Synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 2 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

Journal, Baghdad Science. "Synthesis of Some Heterocyclic Compounds Derived from 2-Mercapto Benzoxazole." Baghdad Science Journal 10, no. 3 (September 1, 2013): 766–78. http://dx.doi.org/10.21123/bsj.10.3.766-778.

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New series of 2-mecapto benzoxazole derivatives (1-20) incorporated into fused to different nitrogen and suphur containing heterocyclic were prepared from 2-meracpto benzoxazole, when treated with hydrazine hydrate to afford 2-hydrazino benzoxazol (1). Compound (1) converted to a variety of pyridazinone andphthalazinone derivatives (2-4) by reaction with different carboxylic anhydride. Also, reaction of (1) with phenyl isothiocyanate and ethyl chloro acetate afforded 3-phenyl-1,3-thiazolidin-2,4-dione-2-(benzoxazole-2-yl-hydrazone) (6). Azomethines (7-10) were prepared through reaction of (1) with aromatic aldehyde, then (7, 8) converted to thaizolidinone derivatives (11, 12). Treatment of (1) with active methylene compounds afforded derivative (13). Reaction of (1) with CS2 and NaOH gave 1,2,4-triazole derivative (14). Treatment of (1) with p-bromophenancyl bromide afforded another 1,2,4-triazole (15). The reaction of 2-mercapto benzoxazole with chloro acetic acid gave (16) followed by refluxing (16) with ortho-amino aniline giving benzimidazol (17). Moreover, the reaction of 2-mercapto benzoxazole with ethyl chloroacetate afforded (18), and then reaction of (18) with thiosemicarbazide and 4% NaOH leads to ring closure giving 1,2,4-triazole derivative (20). All compounds were confirmed by their melting point, FT-IR, UV-Vis spectra and 1H-NMR spectra for some of them.

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3

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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4

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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5

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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6

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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7

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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8

Yang, Po, and Yi Gu. "Synthesis of a novel benzoxazine containing benzoxazole structure." Chinese Chemical Letters 21, no. 5 (May 2010): 558–62. http://dx.doi.org/10.1016/j.cclet.2009.12.012.

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9

Abdelgawad, Mohamed A., Mohammad M. Al-Sanea, Mohamed A. Zaki, Enas I. A. Mohamed, Shabana I. Khan, Babu L. Tekwani, Amar G. Chittiboyina, et al. "New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological Evaluation." Journal of Chemistry 2021 (March 3, 2021): 1–11. http://dx.doi.org/10.1155/2021/6631868.

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Background. Benzoxazole derivatives have different biological activities. 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-2-yl) phenylamine derivatives, 3-benzoxazoloyl acetamide, and butyramide derivatives. Methods. These novel analogs were synthesized in straightforward simple chemistry without any quantitative chromatographic separations in reasonable yields. The biological evaluation of all target compounds as potential antimalarial, antileishmanial, antitrypanosomal, and antimicrobial agents was performed by various well-established cell-based methods. Results. Compounds 6d and 5a showed promising biological screening data. The amidation of 3-benzoxazolyl aniline 1 with the chloroacetyl functional group resulted in a good antimalarial activity and showed moderate inhibitory activities against leishmanial and trypanosomal spp. Moreover, chloroacetyl functionalization of benzoxazolyl aniline serves as a good early goal for constructing and synthesizing new antimicrobial and antiprotozoal agents. The molecular docking study rationalizes the relative inhibitory activity of compound 5a as an antimalarial agent with the deregulation of PfPNP activity which has emerged as a major mechanism of these targets.

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10

Rostom, Sherif, Hesharn Fahmy, and Manal Ssaudi. "Synthesis and in vitro Anti-HIV Screening of Certain 2-(Benzoxazol-2-ylamino)-3H-4-oxopyrimidines." Scientia Pharmaceutica 71, no. 2 (April 14, 2003): 57–74. http://dx.doi.org/10.3797/scipharm.aut-03-08.

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Intensive efforts are underway worldwide to develop chemotherapeutic agents effective against HIV, the etiological agent of AIDS. In this view, it was designed to synthesize and investigate the anti-HIV activity of some new 2-(benzoxazol-2-ylamino)-3H-4-oxopyrimidines following the lead benzoxazole (L 697, 661), which was reported to inhibit the spread of the HIV infection by 95 % in MT4 cell culture. Only the 2-(benzoxazol-2-ylarnino)-6-hydroxy-3H-4-oxopyrdine 8 (NSC 722448) was confirmed to exhibit moderate in vitro anti-HIV activity (percentage of protection 76.83 %).

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11

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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12

Mercer, Frank W., Martin T. McKenzie, Maria Bruma, and Burkhard Schulz. "Synthesis and Characterization of New Fluorinated Poly(Imide Benzoxazole)S." High Performance Polymers 8, no. 3 (September 1996): 395–406. http://dx.doi.org/10.1088/0954-0083/8/3/005.

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We have prepared a series of fluorinated aromatic poly(ether imide benzoxazole)s (PEIBs) and fluorinated aromatic poly(imide benzoxazole)s (PIBs). New PEIBs were prepared by polycondensation of aromatic diamines containing both benzoxazole and hexafluoroisopropylidene groups. New PIBs were prepared by polycondensation of bis( o-aminophenol)s, such as 3,3′-dihydroxybenzidine or 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, with diacid chlorides containing both imide and hexafluoroisopropylidene groups. We have characterized the solubility, film forming ability, thermal stability and dielectric constant of these fluorinated poly(imide benzoxazole)s.

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13

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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14

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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15

Sidra, Lala Rukh, Guofei Chen, Nafeesa Mushtaq, Kai Ma, Beenish Bashir, and Xingzhong Fang. "Processable poly(benzoxazole imide)s derived from asymmetric benzoxazole diamines containing 4-phenoxy aniline: synthesis, properties and the isomeric effect." Polymer Chemistry 9, no. 20 (2018): 2785–96. http://dx.doi.org/10.1039/c8py00382c.

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16

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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17

Ebara, Kazuya, Yuji Shibasaki, and Mitsuru Ueda. "Direct Synthesis of Photosensitive Poly(benzoxazole)." Journal of Photopolymer Science and Technology 14, no. 1 (2001): 55–59. http://dx.doi.org/10.2494/photopolymer.14.55.

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18

Abdelhamid, A. O., V. B. Baghos, and M. M. A. Halim. "Synthesis of Heterocyclic Containing Benzoxazole Moiety." Phosphorus, Sulfur, and Silicon and the Related Elements 183, no. 6 (May 14, 2008): 1313–22. http://dx.doi.org/10.1080/10426500701641262.

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19

Yang, Po, and Yi Gu. "Synthesis of a novel benzoxazine-containing benzoxazole structure and its high performance thermoset." Journal of Applied Polymer Science 124, no. 3 (October 26, 2011): 2415–22. http://dx.doi.org/10.1002/app.35305.

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20

Ishikawa, Nobuo, Mohamed El-said Mustafa, and Akio Takaoka. "Trifluoropyruvic Acid Hydrate in Heterocyclic Synthesis, Part II.: Synthesis of Trifluomethylated Benzoxazine, Benzothiazine, and Benzoxazole Derivatives." HETEROCYCLES 24, no. 3 (1986): 593. http://dx.doi.org/10.3987/r-1986-03-0593.

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21

Datta, Arup. "Dowex 50W: A Green Mild Reusable Catalyst for the Synthesis of 2-Aryl Benzoxazole Derivatives in Aqueous Medium." Oriental Journal Of Chemistry 37, no. 2 (April 30, 2021): 341–47. http://dx.doi.org/10.13005/ojc/370211.

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In this work simple efficient, one pot and environmentally friendly method was developed for the synthesis of 2-Aryl-1H-benzoxazole derivatives at 80º C using ortho-aminophenol and various aldehydes. It has been found that Dowex50W is an effective catalyst to prepare moderate to high yield of a variety of benzoxazole derivatives through a clean and simple process. Aqueous medium, green methodology, rapid reaction, reusability of heterogeneous catalyst are the great advantages of this protocol.

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22

Khunt, Mita D., Vipul C. Kotadiya, Denish J. Viradiya, Bharat H. Baria, and Umed C. Bhoya. "Easy, Simplistic and Green Synthesis of Various Benzimidazole and Benzoxazole Derivatives Using PEG₄₀₀ as a Green Solvent." International Letters of Chemistry, Physics and Astronomy 25 (January 2014): 61–68. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.25.61.

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An improved environmentally benign procedure for the synthesis of various benzimidazole and benzoxazole derivatives using green solvent PEG400. We have optimized the reaction condition and it was found that PEG400 was believed to be best as compared to PEG200, PEG600 and PEG800 at 80 to 85 °C. This method provides a novel route for the synthesis of benzimidazole and benzoxazole derivatives. The main attractive features of this process are a mild reaction conditions, easy workup procedure and good to excellent yield. The structures of all the synthesized compounds were confirmed by 1H NMR, IR, MASS and Elemental Analysis.

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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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24

Yadav, Urmiladevi Narad, Haribhau Shantaram Kumbhar, Saurabh Satish Deshpande, Suban Kumar Sahoo, and Ganapati Subray Shankarling. "Photophysical and thermal properties of novel solid state fluorescent benzoxazole based styryl dyes from a DFT study." RSC Advances 5, no. 53 (2015): 42971–77. http://dx.doi.org/10.1039/c4ra12908c.

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25

Wu, Sheng-Yen, Siu-Ming Yuen, Chen-Chi M. Ma, and Yuan-Li Huang. "Synthesis and properties of aromatic polyimide, poly(benzoxazole imide), and poly(benzoxazole amide imide)." Journal of Applied Polymer Science 113, no. 4 (August 15, 2009): 2301–12. http://dx.doi.org/10.1002/app.30212.

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Alheety, Nuaman. "Synthesis, Characterization and Antimicrobial Activity Study of Some New Substituted Benzoxazole Derivatives." Baghdad Science Journal 16, no. 3 (September 1, 2019): 616. http://dx.doi.org/10.21123/bsj.2019.16.3.616.

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This research included the preparation of 2-mercaptobenzoxazole (N1) by the reaction of ortho-aminophenol with carbon disulfide in an alcoholic potassium hydroxide solution. The 2-mercapto benzoxazole (N1) was then treated with hydrazine to obtain the 2-hydrazino benzoxazole (N2). A number of hydrazones (N3-N5) were prepared through the reaction of N2 with different benzaldehydes. The compound (N6) was also prepared whereby the ring closing of hydrazone (N3) using chloroacetylchloride, while the compound (N7) was prepared by treating 2-hydrazino benzoxazole with acetylacetone. When the compound (N1) was treated with formaldehyde, it afforded the compound (N8). Also, the N9 was obtained from the reaction of N1 with chloroacetic acid in the presence of alcoholic potassium hydroxide. The prepared compounds were characterized using physico-chemical and spectroscopic methods such as melting point, infrared spectroscopy (IR) and the proton nuclear magnetic resonance (1H-NMR). Thereafter, some of the compounds were selected for in vitro antibacterial activity and one of these compounds showed an inhibition effect against gram positive only which is very important because it is considered as specific antibacterial drug.

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Li, Zhengyu, Jingnan Dong, Junwen Wang, Ding-Yah Yang, and Zhiqiang Weng. "Elemental sulfur-promoted one-pot synthesis of 2-(2,2,2-trifluoroethyl)benzoxazoles and their derivatives." Chemical Communications 55, no. 87 (2019): 13132–35. http://dx.doi.org/10.1039/c9cc06822h.

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An elemental sulfur promoted one-pot synthesis of 2-(2,2,2-trifluoroethyl)benzoxazole derivatives from the reaction of o-aminophenols, thiols, and anilines with 2-bromo-3,3,3-trifluoropropene is reported.

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Liu, Xing, Min Liu, Wan Xu, Meng-Tian Zeng, Hui Zhu, Cai-Zhu Chang, and Zhi-Bing Dong. "An environmentally benign and efficient synthesis of substituted benzothiazole-2-thiols, benzoxazole-2-thiols, and benzimidazoline-2-thiones in water." Green Chemistry 19, no. 23 (2017): 5591–98. http://dx.doi.org/10.1039/c7gc02311a.

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29

Chakraborty, Gargi, Rakesh Mondal, Amit Kumar Guin, and Nanda D. Paul. "Nickel catalyzed sustainable synthesis of benzazoles and purines via acceptorless dehydrogenative coupling and borrowing hydrogen approach." Organic & Biomolecular Chemistry 19, no. 33 (2021): 7217–33. http://dx.doi.org/10.1039/d1ob01154e.

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Herein we report nickel-catalyzed sustainable synthesis of a few chosen five-membered fused nitrogen heterocycles such as benzimidazole, purine, benzothiazole, and benzoxazole via acceptorless dehydrogenative functionalization of alcohols.

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30

Tber, Z., M. A. Hiebel, A. El Hakmaoui, M. Akssira, G. Guillaumet, and S. Berteina-Raboin. "Fe–Cu catalyzed synthesis of symmetrical and unsymmetrical diaryl thioethers using 1,3-benzoxazole-2-thiol as a sulfur surrogate." RSC Advances 6, no. 76 (2016): 72030–36. http://dx.doi.org/10.1039/c6ra15335f.

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31

Dadashpour, Sakineh, Tuba T. Küçükkılınç, Ayse Ercan, Seyed J. Hosseinimehr, Nima Naderi, and Hamid Irannejad. "Synthesis and Anticancer Activity of Benzimidazole/Benzoxazole Substituted Triazolotriazines in Hepatocellular Carcinoma." Anti-Cancer Agents in Medicinal Chemistry 19, no. 17 (January 24, 2020): 2120–29. http://dx.doi.org/10.2174/1871520619666190808152051.

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Background: Receptor Tyrosine Kinases (RTK) are the main family of cell surface receptors for growth factors, hormones and cytokines which are responsible for cell growth and differentiation and are considered as an important therapeutic target in cancer. Objective: The aim of this study was to design, synthesise and conduct the biological evaluation of benzimidazole/ benzoxazole substituted triazolotriazines as new anticancer agents. Methods: A series of benzimidazolyl and benzoxazolyl-linked triazolotriazines 8a-e and 9a-e were synthesized as receptor tyrosine kinase inhibitors. Target compounds were evaluated in HGF-induced cell proliferation assay in A549, MCF-7, HepG2 and MDA-MB-231 cancer cells. Results: Hepatocellular carcinoma was the most sensitive cell line towards the tested compounds and 8e was the most potent one on HepG2 cells with an IC50 value of 5.13µM which was close to crizotinib (HepG2 IC50 = 4.35µM) as a standard c-Met kinase inhibitor. c-Met kinase assay of 8e showed that this compound is not capable of inhibiting this enzyme and subsequently molecular docking confirmed the low affinity of 8e towards c- Met active site and its possible anticancer mechanism through VEGFR-2 inhibition. Conclusion: Further in silico predictions revealed that 8e can be a drug candidate with favorable pharmacokinetic properties.

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32

Abakumov, Gleb A., Nikolay O. Druzhkov, Elena N. Egorova, Tatiana N. Kocherova, Andrey S. Shavyrin, and Anton V. Cherkasov. "Intramolecular cyclization–decyclization of new sterically hindered diiminophenol. Synthesis and coordination abilities." RSC Adv. 4, no. 28 (2014): 14495–500. http://dx.doi.org/10.1039/c3ra47669c.

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33

Hong, Nguyen T. T., and Marina E. Trusova. "The Synthesis of Iodbenzimidazoles and Iodbenzoxazoles via Iodination of Arenediazonium Tosylates." Advanced Materials Research 1040 (September 2014): 423–28. http://dx.doi.org/10.4028/www.scientific.net/amr.1040.423.

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The present study describes a synthesis of a series of iodine-benzimidazole and iodine-benzoxazole derivatives. The new and cheap method for its obtaining is developed. All compounds were characterized by physical, chemical, analytical and spectral data.

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34

Oshimoto, Kohei, Hiroaki Tsuji, and Motoi Kawatsura. "Synthesis of benzoxazoles via the copper-catalyzed hydroamination of alkynones with 2-aminophenols." Organic & Biomolecular Chemistry 17, no. 17 (2019): 4225–29. http://dx.doi.org/10.1039/c9ob00572b.

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35

Santos, Fabiano da Silveira, Natália Goedtel Medeiros, Ricardo Ferreira Affeldt, Rodrigo da Costa Duarte, Sidnei Moura, and Fabiano Severo Rodembusch. "Small heterocycles as highly luminescent building blocks in the solid state for organic synthesis." New Journal of Chemistry 40, no. 3 (2016): 2785–91. http://dx.doi.org/10.1039/c5nj02943k.

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36

Maleki, Behrooz, Mehdi Baghayeri, Seyed Mohammad Vahdat, Abbas Mohammadzadeh, and Somaieh Akhoondi. "Ag@TiO2 nanocomposite; synthesis, characterization and its application as a novel and recyclable catalyst for the one-pot synthesis of benzoxazole derivatives in aqueous media." RSC Advances 5, no. 58 (2015): 46545–51. http://dx.doi.org/10.1039/c5ra06618b.

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A Ag@TiO₂ nanocomposite/water as a novel catalytic system is used for the synthesis of benzoxazole derivatives. A shorter reaction time along with high product yield, catalyst stability and recyclability are the merits of this novel protocol.

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37

Jiao, Yang, Guofei Chen, Nafeesa Mushtaq, Haijun Zhou, Xiaoqi Chen, Yantao Li, and Xingzhong Fang. "Synthesis and properties of poly(benzoxazole imide)s derived from two isomeric diamines containing a benzoxazole moiety." Polymer Chemistry 11, no. 11 (2020): 1937–46. http://dx.doi.org/10.1039/c9py01832h.

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38

Rabbani, Mohammad Gulam, Timur Islamoglu, and Hani M. El-Kaderi. "Benzothiazole- and benzoxazole-linked porous polymers for carbon dioxide storage and separation." Journal of Materials Chemistry A 5, no. 1 (2017): 258–65. http://dx.doi.org/10.1039/c6ta06342j.

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The synthesis of highly porous benzoxazole- and benzothiazole-linked organic polymers by condensation routes is reported; the new polymers exhibit high selectivity towards CO₂ capture from gas mixtures.

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39

S. Al-Jawharji, Yaser. "Synthesis of Some Substituted Benzoxazole [3,4-b] imidazoles." JOURNAL OF EDUCATION AND SCIENCE 21, no. 3 (September 1, 2008): 54–61. http://dx.doi.org/10.33899/edusj.2008.56050.

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40

Marchand-Brynaert, Jacqueline, Elodie Lagadic, Frédéric Bruyneel, Noémie Demeyer, Marie-France Hérent, and Yann Garcia. "Phosphonated Benzoxazole Derivatives: Synthesis and Metal-Complexing Properties." Synlett 24, no. 07 (March 18, 2013): 817–22. http://dx.doi.org/10.1055/s-0032-1318500.

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41

Ha, Sie-Tiong, Kok-Leei Foo, and S. Sreehari Sastry. "Synthesis of 5-Chloro-2-(4-tetradecanoyloxybenzylidenamino)benzoxazole." Asian Journal of Chemistry 25, no. 2 (2013): 1175–76. http://dx.doi.org/10.14233/ajchem.2013.13636.

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42

Girán, Levente, Zsuzsanna Gyulai, Sándor Antus, Sándor Berényi, and Attila Sipos. "Synthesis of morphinans with diversely functionalized benzoxazole moieties." Monatshefte für Chemie - Chemical Monthly 141, no. 10 (September 2, 2010): 1135–43. http://dx.doi.org/10.1007/s00706-010-0380-7.

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43

Kim, Darong, Hee Yeon Won, Eun Sook Hwang, Young-Kook Kim, and Hea-Young Park Choo. "Synthesis of benzoxazole derivatives as interleukin-6 antagonists." Bioorganic & Medicinal Chemistry 25, no. 12 (June 2017): 3127–34. http://dx.doi.org/10.1016/j.bmc.2017.03.072.

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44

K. Venkatachalam, T., G. K. Pierens, and D. C. Reutens. "Synthesis and Characterization of Oxazolopyridine and Benzoxazole Derivatives." Letters in Organic Chemistry 7, no. 7 (October 1, 2010): 519–27. http://dx.doi.org/10.2174/157017810793362352.

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45

Pal, Sitaram, Swarnendu Sasmal, Indira Sen, and Roger Hall. "A First Synthesis of Bis(benzoxazole) Natural Products: Nataxazole and AJI9561 via Benzoxazole C–H Activation." Synthesis 47, no. 23 (August 18, 2015): 3711–16. http://dx.doi.org/10.1055/s-0035-1560070.

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46

Felouat, Abdellah, Mathieu Curtil, Julien Massue, and Gilles Ulrich. "Excited-state intramolecular proton transfer (ESIPT) emitters based on a 2-(2′-hydroxybenzofuranyl)benzoxazole (HBBO) scaffold functionalised with oligo(ethylene glycol) (OEG) chains." New Journal of Chemistry 43, no. 23 (2019): 9162–69. http://dx.doi.org/10.1039/c9nj00809h.

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This article describes the multi-step synthesis of 2-(2′-hydroxybenzofuran)benzoxazole (HBBO) derivatives functionalised with one to three oligo(ethylene glycol) (OEG) chains with the goal to allow a good vectorization in aqueous media.

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47

Kuhlmann, Lisa, Rafael Methling, Jasmin Simon, Beate Neumann, Hans-Georg Stammler, Cristian A. Strassert, and Norbert W. Mitzel. "Fluorescent phenoxy benzoxazole complexes of zirconium and hafnium: synthesis, structure and photo-physical behaviour." Dalton Transactions 47, no. 32 (2018): 11245–52. http://dx.doi.org/10.1039/c8dt01757c.

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48

Wu, Yu-Ran, Shu-Ting Ren, Lei Wang, You-Xian Wang, Shu-Hao Liu, Wei-Wei Liu, Da-Hua Shi, and Zhi-Ling Cao. "Synthesis and anticholinesterase activities of novel glycosyl benzoxazole derivatives." Journal of Chemical Research 44, no. 7-8 (January 29, 2020): 363–66. http://dx.doi.org/10.1177/1747519819901251.

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Eight glycosyl benzoxazole derivatives are synthesized by nucleophilic addition reactions of glycosyl isothiocyanate with o-aminophenol in tetrahydrofuran. The reaction conditions are optimized, and good yields (86%–94%) were obtained. The structures of all new products are confirmed by infrared, 1H nuclear magnetic resonance, and high-resolution mass spectrometry (electrospray ionization). In addition, the in vitro cholinesterase inhibitory activities of these new compounds are tested by Ellman’s method.

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49

Kumar, K. Praveen, Y. Prashanthi, G. Rambabu, Md Ataur Rahman, and J. S. Yadav. "Design and Synthesis of 2-Mercapto Benzoxazole coupled Benzyl Triazoles as Anti-inflammatory Agents Targeting COX-2 Enzyme." Asian Journal of Chemistry 32, no. 12 (2020): 3209–18. http://dx.doi.org/10.14233/ajchem.2020.22956.

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In this study, we report the design, synthesis and the biological evaluation of 19 analogues of 2-mercapto benzoxazole coupled benzyl triazoles (BOTs) based on analysis of the binding site and literature of chemical space. These BOTs were evaluated both in vitro and in vivo for their anti-inflammatory activity. Eleven compounds showed less than 10 μM in vitro COX-2 enzyme activities. The most potent analogue among the BOT analogues were BOT15, BOT3 and BOT19 with IC50 3.40 μM, 4.50 μM and 4.57 μM respectively against COX-2. The in vivo anti-inflammatory activity of two BOTs has significantly higher than that of standard drug, ibuprofen. 2-Mercapto benzoxazole coupled benzyl triazoles (BOTs) were also tested for their antioxidant capacity and proved to be an as active scavenger, better than ascorbic acid.

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50

Lu, Yin, Xinye Yu, Corey J. Evans, Shengfu Yang, and Kan Zhang. "Elucidating the role of acetylene in ortho-phthalimide functional benzoxazines: design, synthesis, and structure–property investigations." Polymer Chemistry 12, no. 35 (2021): 5059–68. http://dx.doi.org/10.1039/d1py00850a.

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Novel ortho-phthalimide-benzoxazines containing acetylene have been designed and their corresponding thermosets exhibit excellent thermal stability although the expected benzoxazole cyclization at a much higher temperature did not take place.

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