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Journal articles on the topic 'Oxazoles'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

Murata, Yuki, Masato Kawakubo, Ayumi Maruyama, Mio Matsumura, and Shuji Yasuike. "Synthesis and Optical Properties of N-Arylnaphtho- and Anthra[2,3-d]oxazol-2-amines." Molecules 30, no. 2 (2025): 319. https://doi.org/10.3390/molecules30020319.

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Oxazole, a versatile and significant heteroarene, serves as a bridge between synthetic organic chemistry and applications in the medicinal, pharmaceutical, and industrial fields. Polycyclic aromatic compounds with amino groups substituted at the 2-position of an oxazole, such as 2-aminonaphthoxazoles, are expected to be functional probes, but their synthetic methods are extremely limited. Herein, we describe electrochemical reactions of 3-amino-2-naphthol or 3-amino-2-anthracenol and isothiocyanates in DMSO, using a graphite electrode as an anode and a platinum electrode as a cathode in the pr

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2

Yoshimura, Akira, Akio Saito, Viktor V. Zhdankin, and Mekhman S. Yusubov. "Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions." Synthesis 52, no. 16 (2020): 2299–310. http://dx.doi.org/10.1055/s-0040-1707122.

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Organohypervalent iodine reagents are widely used for the preparation of various oxazolines, oxazoles, isoxazolines, and isoxazoles. In the formation of these heterocyclic compounds, hypervalent iodine species can serve as the activating reagents for various substrates, as well as the heteroatom donor reagents. In recent research, both chemical and electrochemical approaches toward generation of hypervalent iodine species have been utilized. The in situ generated active species can react with appropriate substrates to give the corresponding heterocyclic products. In this short review, we summa

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3

Yamada, Kohei, Naoto Kamimura, and Munetaka Kunishima. "Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid." Beilstein Journal of Organic Chemistry 13 (July 27, 2017): 1478–85. http://dx.doi.org/10.3762/bjoc.13.146.

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A novel method for the synthesis of trisubstituted oxazoles via a one-pot oxazole synthesis/Suzuki–Miyaura coupling sequence has been developed. One-pot formation of 5-(triazinyloxy)oxazoles using carboxylic acids, amino acids and a dehydrative condensing reagent, DMT-MM, followed by Ni-catalyzed Suzuki–Miyaura coupling with boronic acids provided the corresponding 2,4,5-trisubstituted oxazoles in good yields.

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4

Ochędzan-Siodłak, Wioletta, Dawid Siodłak, Karolina Banaś, Katarzyna Halikowska, Sławomir Wierzba, and Karel Doležal. "Naturally Occurring Oxazole Structural Units as Ligands of Vanadium Catalysts for Ethylene-Norbornene (Co)polymerization." Catalysts 11, no. 8 (2021): 923. http://dx.doi.org/10.3390/catal11080923.

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1,3-Oxazole and 4,5-dihydro-1,3-oxazole are common structural motifs in naturally occurring peptides. A series of vanadium complexes were synthesized using VCl3(THF)3 and methyl substituted (4,5-dihydro-1,3-oxazol-2-yl)-1,3-oxazoles as ligands and analyzed using NMR and MS methods. The complexes were found to be active catalysts both in ethylene polymerization and ethylene-norbornene copolymerization. The position of methyl substituent in the ligand has considerable impact on the performance of (co)polymerization reaction, as well as on the microstructure, and thus physical properties of the o

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5

Chiacchio, Maria A., Giuseppe Lanza, Ugo Chiacchio, et al. "Oxazole-Based Compounds As Anticancer Agents." Current Medicinal Chemistry 26, no. 41 (2020): 7337–71. http://dx.doi.org/10.2174/0929867326666181203130402.

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: Heterocyclic compounds represent a significant target for anti-cancer research and drug discovery, due to their structural and chemical diversity. Oxazoles, with oxygen and nitrogen atoms present in the core structure, enable various types of interactions with different enzymes and receptors, favoring the discovery of new drugs. Aim of this review is to describe the most recent reports on the use of oxazole-based compounds in anticancer research, with reference to the newly discovered iso/oxazole-based drugs, to their synthesis and to the evaluation of the most biologically active derivative

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6

Regalla, Venkata Reddy, Rama Krishnam Raju Addada, Venkat Swamy Puli, Abhishek S. Saxena, and Anindita Chatterjee. "HIGHLY EFFICIENT SYNTHESIS OF 2,4-DISUBSTITUTED OXAZOLES THROUGH PALLADIUM/COPPER COMEDIATED DIRECT ARYLATION REACTION." Asian Journal of Pharmaceutical and Clinical Research 11, no. 8 (2018): 511. http://dx.doi.org/10.22159/ajpcr.2018.v11i8.26125.

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Objective: The aim of the present study is to synthesize 2,4-disubstituted oxazoles through palladium/copper comediated direct arylation reaction.Methods: 2,4-disubstituted oxazoles (3a-i) have been synthesized by the reaction of 4-substituted oxazole with aryl bromide in the presence of KOH , CuI and Pd(PPh3)4 in dimethoxyethane. Titled compounds (3a-i) were obtained in good yields using an expedient two-step synthesis of 2,4-disubstituted oxazoles from commercially available starting materialsResults: The structures of the newly synthesized compounds were characterized by Fourier-transform i

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7

Zanakhov, Timur O., Ekaterina E. Galenko, Mariya A. Kryukova, Mikhail S. Novikov, and Alexander A. Khlebnikov. "Isomerization of 5-(2H-Azirin-2-yl)oxazoles: An Atom-Economic Approach to 4H-Pyrrolo[2,3-d]oxazoles." Molecules 26, no. 7 (2021): 1881. http://dx.doi.org/10.3390/molecules26071881.

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An atom economical method for the preparation of variously substituted 4H-pyrrolo[2,3-d]oxazoles was developed on the basis of thermal isomerization of 5-(2H-azirin-2-yl)oxazoles. The latter were prepared by Rh2(oct)4 catalyzed reaction of 2-(3-aryl/heteroaryl)-2-diazoacetyl-2H-azirines with a set of substituted acetonitriles, benzonitriles, acrylonitrile and fumaronitrile. According to DFT calculations the transformation of 5-(2H-azirin-2-yl)oxazole to 4H-pyrrolo[2,3-d]oxazole occurs through the nitrenoid-like transition state to give a 3aH-pyrrolo[2,3-d]oxazole intermediate, followed by 1,5-

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8

He, Yuan, Ting Zheng, Yin-Hui Huang, and Lin Dong. "Rh(iii)-Catalyzed olefination to build diverse oxazole derivatives from functional alkynes." Organic & Biomolecular Chemistry 19, no. 22 (2021): 4937–42. http://dx.doi.org/10.1039/d1ob00507c.

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9

Clark, Adrian D., Uyen T. Ha, Rolf H. Prager, and Jason A. Smith. "High-Temperature Rearrangements of 2-Acylisoxazol-5(2H)-ones and Related Oxazoles." Australian Journal of Chemistry 52, no. 11 (1999): 1029. http://dx.doi.org/10.1071/ch99075.

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2-Acyl-3-arylisoxazol-5(2H)-ones give 2-alkyl(aryl)-4-aryloxazoles in good yields at 540°C under flash vacuum pyrolysis conditions, but at higher temperatures the expected oxazoles are accompanied by increasing amounts of isomeric 2,5-disubstituted oxazoles, as well as anilides and decomposition products of the 2,4-disubstituted oxazole. The rearrangement mechanisms have been studied by the use of 13C labelled substrates and p-substituted 3-arylisoxazolones. The 2,5-disubstituted oxazoles are considered to arise from 1H-azirines, and the anilides from the nitrone ketene isomer of the acylisoxa

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10

Šagud, Ivana, Simona Božić, Željko Marinić, and Marija Šindler-Kulyk. "Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o-vinylstyryl)oxazoles." Beilstein Journal of Organic Chemistry 10 (September 18, 2014): 2222–29. http://dx.doi.org/10.3762/bjoc.10.230.

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Novel cis/trans-4- and cis/trans-5-(2-vinylstyryl)oxazoles have been synthesized by Wittig reactions from the diphosphonium salt of α,α’-o-xylene dibromide, formaldehyde and 4- and 5-oxazolecarbaldehydes, respectively. In contrast, trans-5-(2-vinylstyryl)oxazole has been synthesized by the van Leusen reaction from trans-3-(2-vinylphenyl)acrylaldehyde which is prepared from o-vinylbenzaldehyde and (formylmethylene)triphenylphosphorane. The 4- and 5-(2-vinylstyryl)oxazoles afford, by photochemical intramolecular cycloaddition, diverse fused oxazoline-benzobicyclo[3.2.1]octadienes, which are iden

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11

Glöckner, Steffen, Duc N. Tran, Richard J. Ingham, et al. "The rapid synthesis of oxazolines and their heterogeneous oxidation to oxazoles under flow conditions." Organic & Biomolecular Chemistry 13, no. 1 (2015): 207–14. http://dx.doi.org/10.1039/c4ob02105c.

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12

Apostol, Theodora-Venera, Mariana Carmen Chifiriuc, George Mihai Nitulescu, et al. "In Silico and In Vitro Assessment of Antimicrobial and Antibiofilm Activity of Some 1,3-Oxazole-Based Compounds and Their Isosteric Analogues." Applied Sciences 12, no. 11 (2022): 5571. http://dx.doi.org/10.3390/app12115571.

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In this paper, we report on the antimicrobial activity assessment of 49 compounds previously synthesized as derivatives of alanine or phenylalanine that incorporate a 4-(4-X-phenylsulfonyl)phenyl fragment (X = H, Cl, or Br), namely 21 acyclic compounds (6 × N-acyl-α-amino acids, 1 × N-acyl-α-amino acid ester, and 14 × N-acyl-α-amino ketones) and 28 pentatomic heterocycles from the oxazole-based compound class (6 × 4H-1,3-oxazol-5-ones, 16 × 5-aryl-1,3-oxazoles, and 6 × ethyl 1,3-oxazol-5-yl carbonates). Both in silico and in vitro qualitative and quantitative assays were used to investigate th

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13

Camoutsis, Charalambos. "Steroidal oxazoles, oxazolines, and oxazolidines." Journal of Heterocyclic Chemistry 33, no. 3 (1996): 539–57. http://dx.doi.org/10.1002/jhet.5570330303.

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14

Senadi, Gopal Chandru, Bing-Chun Guo, Wan-Ping Hu, and Jeh-Jeng Wang. "Iodine-promoted cyclization of N-propynyl amides and N-allyl amides via sulfonylation and sulfenylation." Chemical Communications 52, no. 76 (2016): 11410–13. http://dx.doi.org/10.1039/c6cc05138c.

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15

Liu, Can, Zhiming Wang, Lei Wang, Pinhua Li, and Yicheng Zhang. "Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes." Organic & Biomolecular Chemistry 17, no. 41 (2019): 9209–16. http://dx.doi.org/10.1039/c9ob01883b.

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16

Wu, Xia, Xiao Geng, Peng Zhao, Jingjing Zhang, Yan-dong Wu та An-xin Wu. "I2-Promoted formal [3+2] cycloaddition of α-methylenyl isocyanides with methyl ketones: a route to 2,5-disubstituted oxazoles". Chemical Communications 53, № 24 (2017): 3438–41. http://dx.doi.org/10.1039/c6cc10275a.

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An I<sub>2</sub>-promoted formal [3+2] cycloaddition for access to oxazoles has been demonstrated. The salient feature of this approach is unconventional 2,5-disubstituted oxazole formation from isocyanides and ketones rather than 4,5-substituted oxazoline.

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17

Mali, Jaishree K., Balaram S. Takale, and Vikas N. Telvekar. "Readily switchable one-pot 5-exo-dig cyclization using a palladium catalyst." RSC Advances 7, no. 4 (2017): 2231–35. http://dx.doi.org/10.1039/c6ra25857c.

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18

Apostol, Theodora-Venera, Mariana Carmen Chifiriuc, Constantin Draghici, et al. "Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives." Molecules 26, no. 16 (2021): 5107. http://dx.doi.org/10.3390/molecules26165107.

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The multi-step synthesis, physico-chemical characterization, and biological activity of novel valine-derived compounds, i.e., N-acyl-α-amino acids, 1,3-oxazol-5(4H)-ones, N-acyl-α-amino ketones, and 1,3-oxazoles derivatives, bearing a 4-[(4-chlorophenyl)sulfonyl]phenyl moiety are reported here. The structures of the newly synthesized compounds were confirmed by spectral (UV-Vis, FT-IR, MS, 1H- and 13C-NMR) data and elemental analysis results, and their purity was determined by RP-HPLC. The new compounds were assessed for their antimicrobial activity and toxicity to aquatic crustacean Daphnia m

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19

Akula, Mahesh, Yadagiri Thigulla, Connor Davis, Mukund Jha, and Anupam Bhattacharya. "Synthesis of 4-substituted oxazolo[4,5-c]quinolines by direct reaction at the C-4 position of oxazoles." Organic & Biomolecular Chemistry 13, no. 9 (2015): 2600–2605. http://dx.doi.org/10.1039/c4ob02224f.

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Cu(TFA)<sub>2</sub> catalysed synthesis of 4-arylsubstituted oxazolo[4,5-c]quinolines/[1,8] naphthyridines has been described via a modified Pictet–Spengler method, without prefunctionalization of the unreactive 4<sup>th</sup> position of oxazoles.

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20

Belaidi, Salah, and Malika Mellaoui. "Electronic Structure and Physical-Chemistry Property Relationship for Oxazole Derivatives by Ab Initio and DFT Methods." Organic Chemistry International 2011 (September 12, 2011): 1–7. http://dx.doi.org/10.1155/2011/254064.

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The geometric, electronic structure, effect of the substitution, and structure physical-chemistry relationship for oxazoles derivatives have been studied by ab initio and DFT theory. In the present work, the calculated values, namely, net charges, bond lengths, dipole moments, electron affinities, heats of formation, and QSAR properties are reported and discussed in terms of the reactivity of oxazole derivatives.

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21

Yang, Ming, Xue-Cen Xu, Yue Gong, and Yu-Long Zhao. "Rhodium-catalyzed coupling-cyclization reaction of isocyanides and 2-azidophenyloxyacrylates: synthesis of N-(3-substituted benzo[d]oxazol-2(3H)-ylidene)amines and dihydrobenzo[d]oxazoles." Organic Chemistry Frontiers 9, no. 2 (2022): 407–12. http://dx.doi.org/10.1039/d1qo01506k.

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A rhodium-catalyzed coupling cyclization of isocyanides with 2-azidophenyloxyacrylates has been developed. The reaction provides a new method for the synthesis of N-(3-substituted benzo[d]oxazol-2(3H)-ylidene)amines and dihydrobenzo[d]oxazoles.

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22

Fliege, Eckhard, Helmut Dreizler, Michael Meyer, Khalid Iqbal, and John Sheridan. "14N Nuclear Quadrupole Coupling and Methyl Internal Rotation of 2-, 4-, and 5-Methyl Oxazole." Zeitschrift für Naturforschung A 41, no. 4 (1986): 623–36. http://dx.doi.org/10.1515/zna-1986-0407.

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In the following we give an outline of 14N nuclear quadrupole, internal axis method (IAM) methyl internal rotation, and fourth order centrifugal distortion - only needed for extrapolating transition frequencies to higher J values - analyses performed for 2-, 4-, and 5-methyl oxazole.The results are discussed, the three methyl oxazoles being compared with one another and with their common parent, oxazole.

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23

CAMOUTSIS, C. "ChemInform Abstract: Steroidal Oxazoles, Oxazolines, and Oxazolidines." ChemInform 27, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.199650307.

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24

Garg, Ajay Kumar, Ranjan Kumar Singh, Vaibhav Saxena, Saurabh Kr Sinha, and Sanjay Rao. "Synthesis, Characterization, and Anti-inflammatory activity of Some Novel Oxazole Derivatives." Journal of Drug Delivery and Therapeutics 13, no. 1 (2023): 26–28. http://dx.doi.org/10.22270/jddt.v13i1.5719.

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A series of novel oxazole derivatives (A, A1, A2) were synthesized starting from acetone and urea. The compound (A) was obtained by heating it with acetophenone and urea in iodine. Compound (A) on treatment with 4-amino benzaldehyde (Z)-N-(4-amino benzylidine)-4-((E)-Penta-2, 4-diene-2) oxazole-2-amine afforded (A1). Acylation of compound (A) with 4-amino benzoyl chloride to obtain the corresponding N-(4 phenyl oxazole-2- yl)- benzamide (A2). The structures of compounds have been established employing FTIR and 1H-NMR spectral analysis. All oxazole derivatives were evaluated for anti-inflammato

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25

Zhuravlova, Maryna, Nataliya Obernikhina, Stepan Pilyo, Maryna Kachaeva, Oleksiy Kachkovsky, and Volodymyr Brovarets. "In silico binding affinity studies of phenyl-substituted 1,3-oxazoles with protein molecules." Ukr. Bioorg. Acta 2020, Vol. 15, N1 15, no. 1 (2020): 12–19. http://dx.doi.org/10.15407/bioorganica2020.01.012.

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The new model approach of interaction between the pharmacophores with bio-molecules, fragment-to-fragment, is presented. It is a new step of the molecular modeling and takes correctly into consideration not only the spatial complementarity of the interacted molecules but also the contribution of the stacking π-π-electron interaction and hydrogen bonds. As an example, the correct analysis of the interaction of the biological active phenyl-substituted 1,3-oxazoles with protein fragments is performed. It was shown that the length and energy of the hydrogen bond uniquely depend on the chemical con

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26

Brusnakov, Mykhailo, Oleksandr Golovchenko, Lyudmyla Potikha, and Volodymyr Brovarets. "1,3-Oxazoles as precursors of phosphorylated amino acids and peptidomimetics." Ukr. Bioorg. Acta 2022, Vol. 17, N1 17, no. 1 (2022): 72–80. http://dx.doi.org/10.15407/bioorganica2022.01.072.

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The design and development of new phosphorus-containing amino acids and peptidomimetics have been attracting considerable attention due to their value as intermediates in the synthesis of biologically active compounds and the prospects for further pharmacological applications. 1,3-Oxazole derivatives, as masked peptides, constitute an important group of amino acid precursors that are widely used in contemporary organic synthesis. This review presents the 1,3-oxazole-based synthetic strategies of phosphorylated amino acids and peptides that have been published in both journal and patent literat

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27

Kenari, Marziyeh E., Joshua I. Putman, Ravi P. Singh, et al. "Enantiomeric Separation of New Chiral Azole Compounds." Molecules 26, no. 1 (2021): 213. http://dx.doi.org/10.3390/molecules26010213.

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Twelve new azole compounds were synthesized through an ene reaction involving methylidene heterocycles and phenylmaleimide, producing four oxazoles, five thiazoles, and one pyridine derivative, and ethyl glyoxylate for an oxazole and a thiazole compound. The twelve azoles have a stereogenic center in their structure. Hence, a method to separate the enantiomeric pairs, must be provided if any further study of chemical and pharmacological importance of these compounds is to be accomplished. Six chiral stationary phases were assayed: four were based on macrocyclic glycopeptide selectors and two o

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28

Shablykin, Oleh, Egor Herasymov, Olga Shablykina, and Andrii Kozytsky. "Synthesis of 2-R-5-amino-4-(1H-tetrazol-5-yl)-1,3-oxazoles from 2-R-5-amino-1,3-oxazole-4-carbonitriles." Current Chemistry Letters 14, no. 1 (2025): 233–38. http://dx.doi.org/10.5267/j.ccl.2024.6.003.

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This short communication reports about new 5-amino-4-(1H-tetrazol-5-yl)-1,3-oxazoles which were synthesized by [3+2] cycloaddition of 2-R-5-amino-1,3-oxazole-4-carbonitriles and trimethylsilyl azide with dibutyltin oxide present. The reaction conditions provided high yields of the products, and were tolerant to some active functional fragments in the oxazole substituents (amino, amido, and hydroxy group). In the case of 2-((4-cyano-2-phenyloxazol-5-yl)amino)-N-methylacetamide the by-product (N-((1-(2-(methylamino)-2-oxoethyl)-1H-tetrazol-5-yl)(1H-tetrazol-5-yl)methyl)-benzamide) was formed tog

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29

Meyers, A. I., and Francis Tavares. "The oxidation of 2-oxazolines to 1,3-oxazoles." Tetrahedron Letters 35, no. 16 (1994): 2481–84. http://dx.doi.org/10.1016/s0040-4039(00)77149-8.

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30

Blancou, Wafa, Badr Jismy, Soufiane Touil, Hassan Allouchi, and Mohamed Abarbri. "Simple and Expedient Access to Novel Fluorinated Thiazolo- and Oxazolo[3,2-a]pyrimidin-7-one Derivatives and Their Functionalization via Palladium-Catalyzed Reactions." Molecules 27, no. 9 (2022): 3013. http://dx.doi.org/10.3390/molecules27093013.

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An efficient, versatile, and one-pot method for the preparation of novel fluorinated thiazolo- and oxazolo[3,2-a]pyrimidin-7-ones is described from 2-aminothiazoles or 2-amino-oxazoles and fluorinated alkynoates. This transformation, performed under transition-metal-free conditions, offers new fluorinated cyclized products with good to excellent yields. Moreover, the functionalization of these N-fused scaffolds via the Suzuki-Miyaura and Sonogashira cross-coupling reactions led to the synthesis of highly diverse thiazolo- and oxazolo[3,2-a]pyrimidin-7-ones.

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31

Bahrieieva, Oksana S., Oleksandr V. Golovchenko, Oksana I. Golovchenko, Victor V. Zhirnov, and Volodymyr S. Brovarets. "New phosphorylated 5-(hydroxyalkylamino)-1,3-oxazoles as potential anticancer agents." Ukr. Bioorg. Acta 2023, Vol. 18, N1 18, no. 1 (2023): 32–41. http://dx.doi.org/10.15407/bioorganica2023.01.032.

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Eight new phosphorylated 5-(hydroxyalkylamino)-1,3-oxazoles were designed and tested for their ability to inhibit cancer cell growth. These compounds were evaluated against complete human tumor cell lines NCI-60. Only three compounds showed antitumor activity in the single dose assay, which were taken in the five dose assay. Compounds 7 and 8 showed the same average antiproliferative activity and cytotoxicity against sensitive cell lines of the general panel. However, compound 8 showed cytotoxicity to more lines than 7. By all parameters, these compounds were more active than compounds 5. Comp

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32

Slobodyanyuk, Evgeniy Y., Oleksiy S. Artamonov, Irene B. Kulik, Eduard Rusanov, Dmitriy M. Volochnyuk, and Oleksandr O. Grygorenko. "A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles." Heterocyclic Communications 24, no. 1 (2018): 11–17. http://dx.doi.org/10.1515/hc-2017-0235.

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Abstract A convenient four-step approach to the synthesis of (S)-4-alkyl-2-(pyrrolidin-2-yl)oxazoles starting from l-Boc-proline inspired by naturally occurring oxazole-containing peptidomimetics is described. The key step is the cyclization of 1-Boc-N-(1-oxoalkan-2-yl)pyrrolidine-2-carboxamides – aldehyde intermediates which demonstrate low to moderate stability – under Appel reaction conditions. This method furnishes the target compounds with more than 98% ee and in a 17–51% overall yield and has been used at up to a 45-g scale.

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33

García-Ramírez, Verónica G., Abel Suarez-Castro, Ma Guadalupe Villa-Lopez, Erik Díaz-Cervantes, Luis Chacón-García, and Carlos J. Cortes-García. "Synthesis of Novel Acylhydrazone-Oxazole Hybrids and Docking Studies of SARS-CoV-2 Main Protease." Chemistry Proceedings 3, no. 1 (2020): 1. http://dx.doi.org/10.3390/ecsoc-24-08329.

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A novel synthetic strategy to obtain acylhydrazone-oxazole hybrids in three-step reactions in moderate to good yields is reported. The key step reaction consists in a Van Leusen reaction using a bifunctional component of both an aldehyde and a functional group. The target molecules were evaluated via in-silico by molecular docking with the main protease enzyme of SARS-Cov-2, where two acyl hydralazine-oxazoles yielded good predicted free energy values in comparison to the co-crystalized ligand.

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34

Yang, Feihu, Xiaojie Zheng, Qiong Hu, Yimin Hu, Yu Lei, and Wenjing Zhu. "Epoxyanthracene Derivatives and Dicarbonylation on Benzene Ring via Hexadehydro-Diels–Alder (HDDA) Derived Benzynes with Oxazoles." Synthesis 54, no. 04 (2021): 1125–33. http://dx.doi.org/10.1055/a-1659-8167.

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AbstractA capture reaction of hexadehydro-Diels–Alder (HDDA) derived benzyne with various substituted oxazoles is reported. With methyl, hydrogen, or phenyl as the substituent at 2-position of oxazole, tetraynes afforded epoxyanthracene derivatives or underwent dicarbonylation on benzene ring. The reaction does not require any catalyst or additive. The mechanism behind the reaction was investigated. The obtained polycyclic product structure has potential application value in optoelectronic materials. The availability of dicarbonylated arene implies the uniqueness of HDDA benzyne reaction compa

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35

Doyle, Kevin J., and Christopher J. Moody. "The rhodium carbenoid route to oxazoles. Synthesis of 4-functionalised oxazoles; Three step preparation of a bis-oxazole." Tetrahedron 50, no. 12 (1994): 3761–72. http://dx.doi.org/10.1016/s0040-4020(01)90396-5.

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36

Rostovskii, Nikolai V., Mikhail S. Novikov, Alexander F. Khlebnikov, Galina L. Starova та Margarita S. Avdontseva. "Azirinium ylides from α-diazoketones and 2H-azirines on the route to 2H-1,4-oxazines: three-membered ring opening vs 1,5-cyclization". Beilstein Journal of Organic Chemistry 11 (2 березня 2015): 302–12. http://dx.doi.org/10.3762/bjoc.11.35.

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Strained azirinium ylides derived from 2H-azirines and α-diazoketones under Rh(II)-catalysis can undergo either irreversible ring opening across the N–C2 bond to 2-azabuta-1,3-dienes that further cyclize to 2H-1,4-oxazines or reversibly undergo a 1,5-cyclization to dihydroazireno[2,1-b]oxazoles. Dihydroazireno[2,1-b]oxazoles derived from 3-aryl-2H-azirines and 3-diazoacetylacetone or ethyl diazoacetoacetate are able to cycloadd to acetyl(methyl)ketene generated from 3-diazoacetylacetone under Rh(II) catalysis to give 4,6-dioxa-1-azabicyclo[3.2.1]oct-2-ene and/or 5,7-dioxa-1-azabicyclo[4.3.1]de

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37

Nyce, P., M. S. Puar, D. Gala, and R. S. Jaret. "A novel acyclic addition of ketenes to oxazoles/oxazolines." Journal of Heterocyclic Chemistry 24, no. 2 (1987): 505–8. http://dx.doi.org/10.1002/jhet.5570240239.

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Bagley, Mark C., Richard T. Buck, S. Lucy Hind, and Christopher J. Moody. "Synthesis of functionalised oxazoles and bis-oxazoles 1." Journal of the Chemical Society, Perkin Transactions 1, no. 3 (1998): 591–600. http://dx.doi.org/10.1039/a704093h.

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Gao, Juan-Juan, Long-Hui Wu, Shu-Qin Yu, et al. "Synthesis of Oxazoles Containing CF3-Substituted Alcohol Unit via Tandem Cycloisomerization/Hydroxyalkylation from N-Propargylamides with Trifluoropyruvates." Molecules 29, no. 24 (2024): 5848. https://doi.org/10.3390/molecules29245848.

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Oxazoles are important five-membered heterocycles that contain both nitrogen and oxygen atoms. Due to their wide range of biological activities, many oxazoles demonstrate potential for extensive application in various fields, including medicinal chemistry. Trifluoromethyl carbinol, an important pharmacophore, contains both trifluoromethyl and hydroxyl groups and is common in molecules with important biological activities. Constructing oxazoles that contain a trifluoromethyl carbinol unit is undoubtedly important and valuable for expanding the chemical space in drug discovery. In this study, a

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Dang, Qun, Srinivas Rao Kasibthatla, Tao Jiang, et al. "Oxazole phosphonic acids as fructose 1,6-bisphosphatase inhibitors with potent glucose-lowering activity." MedChemComm 2, no. 4 (2011): 287–90. http://dx.doi.org/10.1039/c0md00269k.

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Phosphonic acid-containing oxazoles were discovered as potent inhibitors of fructose 1,6-bisphosphatase. Several oxazoles demonstrated significant glucose-lowering activity in rats after intravenous dosing.

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DOYLE, K. J., and C. J. MOODY. "ChemInform Abstract: The Rhodium Carbenoid Route to Oxazoles. Synthesis of 4-Functionalised Oxazoles: Three Step Preparation of a Bis-oxazole." ChemInform 25, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199431141.

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Pandey, Nagendra Kumar, Ashok Kumar, Rashmi Sharma, Deepika Geedkar, and Pratibha Sharma. "You are entitled to access the full text of this document Synthesis and molecular docking studies of pyrazolo-oxazole derivatives as potential inhibitors of P. gingivalis heme-binding protein." Current Chemistry Letters 14, no. 3 (2025): 579–96. https://doi.org/10.5267/j.ccl.2025.2.004.

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The present paper elicits the studies on synthesis and potential pharmacological applications of pyrazolo-oxazole heterocyclic scaffolds. The synthesized compounds were characterized by different spectroanalytical tools including 1H NMR, 13C NMR, and FTIR techniques, followed by molecular docking-based biological interaction studies. Synthesized pyrazolo-oxazoles (8a–f) were docked against the heme-binding protein of P. gingivalis, an oral pathogen, responsible for a number of diseases. Among the synthesized heterocycles, compounds 8e and 8f showed better docking scores compared to the markete

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BAGLEY, M. C., R. T. BUCK, S. L. HIND, and C. J. MOODY. "ChemInform Abstract: Synthesis of Functionalized Oxazoles and Bis-Oxazoles." ChemInform 29, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199826160.

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Roberto, Dominique, and Howard Alper. "Octacarbonyldicobalt induced conversion of 1,2-diaroyldiaziridines into dihydro-oxazoles (oxazolines)." Journal of the Chemical Society, Chemical Communications, no. 3 (1987): 212. http://dx.doi.org/10.1039/c39870000212.

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Klein, Robert F. X., Václav Horák, and Godfrey A. S. Baker. "Novel Dehydrogenation of 2,5-Diaryl Substituted ∆2-Oxazolines to Oxazoles." Collection of Czechoslovak Chemical Communications 58, no. 7 (1993): 1631–35. http://dx.doi.org/10.1135/cccc19931631.

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The dehydrogenation of various 2,5-diaryl substituted ∆2-oxazolines with either Br2/LiBr/CaCO3 (molar ratio 1.05 : 2 : 3) or CuBr2/LiBr/CaCO3 (molar ratio 2 : 1 : 3) in refluxing o-dichlorobenzene gives the corresponding oxazole up to 87% yield. Free radical benzylic bromination followed by dehydrobromination is the expected dehydrogenation mechanism. The successful application of the reagent combination for this transformation is in contrast to standard dehydrogenation reagents, including N-bromosuccinimide, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, chloranil, NiO2 and active γ-MnO2.

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MEYERS, A. I., and F. TAVARES. "ChemInform Abstract: The Oxidation of 2-Oxazolines to 1,3-Oxazoles." ChemInform 25, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199433167.

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da Silva Filho, Antonio João, Lucinêz da Cruz Dantas, and Otávio Luís de Santana. "Diradicalar Character and Ring Stability of Mesoionic Heterocyclic Oxazoles and Thiazoles by Ab Initio Mono and Multi-Reference Methods." Molecules 25, no. 19 (2020): 4524. http://dx.doi.org/10.3390/molecules25194524.

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Mesoionics are neutral compounds that cannot be represented by a fully covalent or purely ionic structure. Among the possible mesomeric structures of these compounds are the diradical electronic configurations. Theoretical and experimental studies indicate that some mesoionic rings are unstable, which may be related to a significant diradical character, that until then is not quantified. In this work, we investigated the diradical character of four heterocycles: 1,3-oxazol-5-one, 1,3-oxazol-5-thione, 1,3-thiazole-5-one, and 1,3-thiazole-5-thione. The oxazoles are known to be significatively le

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García-Ramírez, Verónica G., Claudia Contreras-Celedón, Gabriela Rodriguez-García, Luis Chacón-García, and Carlos J. Cortes-García. "Synthesis of 1,3-Oxazoles via Van Leusen Reaction in a Pressure Reactor and Preliminary Studies of Cations Recognition." Proceedings 41, no. 1 (2019): 7. http://dx.doi.org/10.3390/ecsoc-23-06463.

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Six 1,3-oxazoles were synthetized in moderate to good yields by Van Leusen reaction in a pressure reactor. The methodology allowed to decrease the reaction times reported in the literature from hours to 20 min. In addition, preliminary qualitative recognition of cations with some synthetized oxazoles such as Hg2+, Ni2+, Zn2+, Ag+, Cu2+, Pb2+ was done and a “turn off” effect was observed with Ni2+. Finally, the 1,3-oxazoles could be of biological relevance because they are considered privileged nucleus in medicinal chemistry and therefore will be useful to obtain pharmacophoric hybrid molecules

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Rossa, Thaís A., Nícolas S. Suveges, Marcus M. Sá, David Cantillo, and C. Oliver Kappe. "Continuous multistep synthesis of 2-(azidomethyl)oxazoles." Beilstein Journal of Organic Chemistry 14 (February 23, 2018): 506–14. http://dx.doi.org/10.3762/bjoc.14.36.

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An efficient three-step protocol was developed to produce 2-(azidomethyl)oxazoles from vinyl azides in a continuous-flow process. The general synthetic strategy involves a thermolysis of vinyl azides to generate azirines, which react with bromoacetyl bromide to provide 2-(bromomethyl)oxazoles. The latter compounds are versatile building blocks for nucleophilic displacement reactions as demonstrated by their subsequent treatment with NaN3 in aqueous medium to give azido oxazoles in good selectivity. Process integration enabled the synthesis of this useful moiety in short overall residence times

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Babaev, E. V. "Pyrroles from oxazoles." Chemistry of Heterocyclic Compounds 48, no. 1 (2012): 59–72. http://dx.doi.org/10.1007/s10593-012-0970-x.

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