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Journal articles on the topic '3-oxazole'

Author: Grafiati

Published: 7 June 2025

Last updated: 2 August 2025

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1

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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2

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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3

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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4

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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5

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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6

Mukhtorov, Loik G., Maria B. Nikishina, Evgenia V. Ivanova, Yury M. Atroschenko, Irina V. Shahkeldyan, and Konstantin I. Kobrakov. "Study of the biological activity of anionic adduts of 5,7-dinitrobenz[d]oxazole." Butlerov Communications 58, no. 5 (2019): 32–38. http://dx.doi.org/10.37952/roi-jbc-01/19-58-5-32.

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In this paper, we studied the effect of anionic adducts of 5,7-dinitrobenz[d]oxazole on the sowing properties of wheat seeds (germination energy and germination), the growth rate of wheat shoots, amylase activity in the roots and shoots of wheat. The evaluation of the toxicity of the tested compounds was carried out using the GUSAR on-line computer program. A prediction was made of bioaccumulation factor (BCF), the average lethal concentration for daphnia and minnow (LD50), the concentration of half-maximal growth inhibition (IGC50) and the acute toxicity indicators (LD50) for rats with differ

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7

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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8

Ivanova, Yordanka B., Filip E. Svetoslavov, and Ognyan I. Petrov. "(E)-5-(3-Oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)benzo[d]oxazol-2(3H)-one." Molbank 2024, no. 3 (2024): M1866. http://dx.doi.org/10.3390/m1866.

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The title compound, (E)-5-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)benzo[d]oxazol-2(3H)-one, was synthesized by the acid- and base-catalyzed aldol condensation of 2-oxo-2,3-dihydrobenzo[d]oxazole-5-carbaldehyde and 3,4,5-trimethoxyacetophenone. The structure of the target compound was confirmed using 1H NMR, 13C NMR, HRMS, and elemental analysis.

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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

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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11

Zreigh, Mohamed M., Harry Adams, Richard F. W. Jackson, and Craig C. Robertson. "The first crystal structure of the pyrrolo[1,2-c]oxazole ring system." Acta Crystallographica Section E Crystallographic Communications 75, no. 9 (2019): 1336–38. http://dx.doi.org/10.1107/s2056989019011095.

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The title compound, C7H4F3NO2, 3-trifluoromethyl-1H-pyrrolo[1,2-c]oxazol-1-one, is the first crystal structure of the pyrrolo[1,2-c]oxazole ring system: the fused ring system is almost planar (r.m.s. deviation = 0.006 Å). In the crystal, weak C—H...O and C—H...F hydrogen bonds link the molecules into [001] chains and π–π stacking interactions consolidate the structure.

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12

Burade, Sachin S., Sushil V. Pawar, Tanmoy Saha та ін. "Sugar-derived oxazolone pseudotetrapeptide as γ-turn inducer and anion-selective transporter". Beilstein Journal of Organic Chemistry 15 (14 жовтня 2019): 2419–27. http://dx.doi.org/10.3762/bjoc.15.234.

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The intramolecular cyclization of a C-3-tetrasubstituted furanoid sugar amino acid-derived linear tetrapeptide afforded an oxazolone pseudo-peptide with the formation of an oxazole ring at the C-terminus. A conformational study of the oxazolone pseudo-peptide showed intramolecular C=O···HN(II) hydrogen bonding in a seven-membered ring leading to a γ-turn conformation. This fact was supported by a solution-state NMR and molecular modeling studies. The oxazolone pseudotetrapeptide was found to be a better Cl−-selective transporter for which an anion–anion antiport mechanism was established.

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13

Maľučká, Lucia Ungvarská, and Mária Vilková. "Spectral Assignment in the [3 + 2] Cycloadditions of Methyl (2E)-3-(acridin-4-yl)-prop-2-enoate and 4-[(E)-2-Phenylethenyl]acridin with Unstable Nitrile N-Oxides." Molecules 29, no. 12 (2024): 2756. http://dx.doi.org/10.3390/molecules29122756.

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The investigation of cycloaddition reactions involving acridine-based dipolarophiles revealed distinct regioselectivity patterns influenced mainly by the electronic factor. Specifically, the reactions of methyl-(2E)-3-(acridin-4-yl)-prop-2-enoate and 4-[(1E)-2-phenylethenyl]acridine with unstable benzonitrile N-oxides were studied. For methyl-(2E)-3-(acridin-4-yl)-prop-2-enoate, the formation of two regioisomers favoured the 5-(acridin-4-yl)-4,5-dihydro-1,2-oxazole-4-carboxylates, with remarkable exclusivity in the case of 4-methoxybenzonitrile oxide. Conversely, 4-[(1E)-2-phenylethenyl]acridi

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14

Balakrishnan, B., C. Praveen, P. R. Seshadri, and P. T. Perumal. "5-(3-Methylphenyl)-3-phenyl-1,2-oxazole." Acta Crystallographica Section E Structure Reports Online 67, no. 7 (2011): o1575. http://dx.doi.org/10.1107/s1600536811020198.

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15

Balakrishnan, B., C. Praveen, P. R. Seshadri, and P. T. Perumal. "5-(3-Methoxyphenyl)-3-phenyl-1,2-oxazole." Acta Crystallographica Section E Structure Reports Online 69, no. 4 (2013): o597. http://dx.doi.org/10.1107/s160053681300740x.

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16

Tsygankova, V.A., Ya.V. Andrusevich, O.I. Shtompel, A.M. Kornienko, V.S. Brovarets, and S.G. Pilyo. "Acceleration of vegetative growth of wheat (Triticum aestivum L.) using [1,3]oxazolo[5,4-d]pyrimidine and N-sulfonyl substituted 1,3-oxazole." Pharmaceutical and Chemical Journal 5, no. 2 (2018): 167–75. https://doi.org/10.5281/zenodo.13904610.

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Wheat (<em>Triticum aestivum</em> L.) is an important cereal crop cultivated in the most economically developed coutries. The elaboration of new effective growth regulators for intensification of seed germination stage and vegetative growth of wheat is an actual problem for modern agriculture. In our work the comparative analysis of regulating activity of low molecular weight heterocyclic compounds, derivatives of [1,3]oxazolo[5,4-<em>d</em>]pyrimidine and N-sulfonyl substituted of 1,3-oxazole, and plant hormones auxins IAA (1<em>H</em>-Indol-3-ylacetic acid) and NAA (1-Naphthylacetic acid) on

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17

Apostol, Theodora-Venera, Luminita Gabriela Marutescu, Constantin Draghici та ін. "Synthesis and Biological Evaluation of New N-Acyl-α-amino Ketones and 1,3-Oxazoles Derivatives". Molecules 26, № 16 (2021): 5019. http://dx.doi.org/10.3390/molecules26165019.

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In order to develop novel bioactive substances with potent activities, some new valine-derived compounds incorporating a 4-(phenylsulfonyl)phenyl fragment, namely, acyclic precursors from N-acyl-α-amino acids and N-acyl-α-amino ketones classes, and heterocycles from the large family of 1,3-oxazole-based compounds, were synthesized. The structures of the new compounds were established using elemental analysis and spectral (UV-Vis, FT-IR, MS, NMR) data, and their purity was checked by reversed-phase HPLC. The newly synthesized compounds were evaluated for their antimicrobial and antibiofilm acti

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18

Zhang, Qi, Yao Huang, Heran Cao, Fangyi Gong, Qingye Gan, and Beibei Mao. "Synthesis of tert-butyl 3-(2-(4-amino-3-(2-aminobenzo[d]oxazole-5-yl)-1H-pyrazole[3,4-d] pyrimidine-1-yl) ethoxy) propionate." Highlights in Science, Engineering and Technology 2 (June 22, 2022): 330–36. http://dx.doi.org/10.54097/hset.v2i.591.

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Tert-butyl 3-(2-(4-amino-3-(2-aminobenzo[d]oxazol-5-yl)-1H-pyrazole[3,4-d] pyrimidine-1-yl) ethoxy) propionate plays an important role in the whole synthesis route as an intermediate of target mTOR targeted PROTAC molecule PRO1. In this experiment, palladium catalyzed Suzuki reaction was used, the target compound tert-butyl 3-(2-(4-amino-3-(2-aminobenzo[d]oxazol-5-yl)-1H-pyrazole[3,4-d]pyrimidine-1-yl)ethoxy)propionate (compound 3) was synthesized from 5-(4,4,5,5-tetramethyl-1,3,2-dioxobenzaldehyde-2-yl) benzo[d]oxazole-2-amine (compound 1) and 3-(2-{4-amino-3-iodine-1H-pyrazole[3,4-d]pyrimidi

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19

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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20

Khokhlov, Alexander L., Ilya I. Yaichkov, Anton А. Shetnev, et al. "Identification and synthesis of metabolites of the new antiglaucoma drug." Research Results in Pharmacology 10, no. 1 (2023): 53–66. http://dx.doi.org/10.18413/rrpharmacology.10.431.

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Introduction: The determination of biotransformation products is an essential part of the preclinical trial of original medicines. These studies have not been conducted before for the new drug 5-[5-(trifluoromethyl)-1,2-oxazole-3-yl]-furan-2-sulfonamide. Identification and synthesis of metabolite substances are necessary for subsequent tests of bioavailability, linearity of pharmacokinetics, accumulation, distribution and excretion. Materials and methods: The study was carried out on Wistar rats and rabbits of the Soviet Chinchilla breed. The substance of the drug was administered to animals i

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21

Muzychka, Oksana, Olexandr Kobzar, Oleg Shablykin, Volodymyr Brovarets, and Andriy Vovk. "5-Substituted N-(9H-purin-6-yl)-1,2-oxazole-3-carboxamides as xanthine oxidase inhibitors." Ukr. Bioorg. Acta 2020, Vol. 15, N1 15, no. 1 (2020): 20–25. http://dx.doi.org/10.15407/bioorganica2020.01.020.

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Synthetic 6-substituted purine derivatives are known to exhibit diverse bioactivity. In this paper, a series of N-(9H-purin-6-yl)-1,2-oxazole-3-carboxamide derivatives were synthesized and evaluated in vitro against xanthine oxidase, an enzyme of purine catabolism. The introduction of aryl substituent at position 5 of the oxazole ring was found to increase the inhibition efficiency. Some of the inhibitors containing 5-substituted isoxazole and purine moieties were characterized by IC50 values in the nanomolar range. According to the kinetic data, the most active N-(9H-purin-6-yl)-5-(5,6,7,8-te

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22

Pan, Mei-Ling, Yang-Hui Luo, and Jin-Feng Li. "5-Methyl-1,2-oxazole-3-carboxylic acid." Acta Crystallographica Section E Structure Reports Online 67, no. 10 (2011): o2545. http://dx.doi.org/10.1107/s160053681103532x.

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23

Cores, Ángel, Mercedes Villacampa, and J. Carlos Menéndez. "2-(3-Bromophenyl)imidazo[2,1-b]oxazole." Molbank 2023, no. 2 (2023): M1616. http://dx.doi.org/10.3390/m1616.

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The microwave-assisted reaction of 2-nitroimidazole with 3-bromophenacyl bromide in the presence of potassium carbonate as a base and dimethylformamide as a solvent afforded 2-(3-bromophenyl)imidazo[2,1-b]oxazole. The formation of this compound was explained via a domino mechanism comprising an initial N-alkylation reaction of the imidazole substrate, followed by the base-promoted deprotonation of the position adjacent to the carbonyl to give an enolate anion that finally cyclizes via an intramolecular SNAr reaction, with the loss of the nitro group as potassium nitrite. Then, the proposed 1-(

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24

Szabó, Tímea, Róbert Kormány, András Dancsó, Balázs Volk, and Mátyás Milen. "Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–C." SynOpen 03, no. 04 (2019): 148–56. http://dx.doi.org/10.1055/s-0039-1690336.

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Pimprinols A, B, and C are bacterial 5-(3-indolyl)oxazole alkaloids that have been isolated from Streptomyces sp. Lv3–13. In this paper, we report a new synthesis of pimprinol A and the first total synthesis of pimprinol B and pimprinol C. In addition, antipodes of the naturally occurring pimprinols A and C, as well as the racemates of these two alkaloids were also prepared. In the pivotal step, the 1,3-oxazole ring was constructed by a Nicolaou’s modified Robinson–Gabriel cyclization.

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Chojnacka, Maja W., Jeanette A. Adjei, Alan J. Lough, Guerino G. Sacripante та Robert A. Gossage. "Transition metal complexes of monodentate 2-oxazolines containing long chain alkyl groups. The crystal structure of trans-PdCl2(κ1-N-rac-2-heptadecyl-4,5-dihydro-5-methyl-2-oxazole)2". Zeitschrift für Naturforschung B 75, № 4 (2020): 371–77. http://dx.doi.org/10.1515/znb-2019-0212.

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AbstractThe synthesis, characterisation and properties of several divalent metal complexes (Co, Ni, Pd) containing 2-oxazoline ligands L1–L3, appended with long chain alkyl and/or ester groups, is reported. The X-ray crystal structure aspects of one such complex, trans-PdCl2(rac-2-heptadecyl-4,5-dihydro-5-methyl-2-oxazole)2 (i.e. PdCl2(L1)2: 3), is described. This latter material contains one of the longest alkyl chains to be crystallographically characterised appended to an oxazoline ligand. The complexes reported herein represent the first transition metal derivatives of these high molecular

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26

Kuneš, Jiří, Vojtěch Balšánek, Milan Pour, and Vladimír Buchta. "Synthesis and Antifungal Activity Evaluation of 3-Hetaryl-2,5-dihydrofuran-2-ones. An Unusual Fragmentation of the Oxazole Ring via 2,3-Selenoxide Shift." Collection of Czechoslovak Chemical Communications 66, no. 12 (2001): 1809–30. http://dx.doi.org/10.1135/cccc20011809.

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In continuing the studies on the synthesis and evaluation of antifungal activity of the analogues of (-)incrustoporine, the replacement of the phenyl moiety at C3 of the furanone ring with a hetaryl substituent was considered. Thus, a series of 5-alkyl-3-hetaryl-2,5-dihydrofuran-2-ones with the thienyl, furyl and thiazolyl moieties attached to C3 was synthesized, and the compounds subjected to antifungal activity screening. In the preparation of compounds containing the oxazolyl fragment, the [2,3]-sigmatropic rearrangement led to the fragmentation of the oxazole ring, resulting in the formati

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27

Tsygankova, V.A., Ya.V. Andrusevich, O.I. Shtompel, S.G. Pilyo, A.M. Kornienko, and V.S. Brovarets. "Using of [1,3]oxazolo[5,4-d]pyrimidine and N-sulfonyl substituted of 1,3-oxazole to improve the growth of soybean seedlings." Chemistry Research Journal 3, no. 2 (2018): 165–73. https://doi.org/10.5281/zenodo.13923631.

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The effect of the chemical low molecular weight heterocyclic compounds, derivatives of [1,3]oxazolo[5,4-<em>d</em>]pyrimidine and N-sulfonylsubstituted of 1,3-oxazole on stimulation of root and shoot growth of soybean seedlings (<em>Glycine max </em>L.) cultivar Valuta was studied. The growth regulating activity of the heterocyclic compounds derivatives of [1,3]oxazolo[5,4-<em>d</em>]pyrimidine and N-sulfonyl substituted of 1,3-oxazole was compared with the growth regulating activity of the plant hormone auxin NAA (1-Naphthylacetic acid). It was found that the chemical heterocyclic compounds u

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28

Shoghpour, Samad, Amir Keykha, Hadi Amiri Rudbari, et al. "5-Amino-3-methyl-1,2-oxazole-4-carbonitrile." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (2012): o2530. http://dx.doi.org/10.1107/s1600536812032667.

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In the title compound, C5H5N3O, the isoxazole ring is essentially planar, with a maximum deviation of 0.007 (1) Å from the least-squares plane. The N atom of the amine group exhibitssp2character (sum of bond angles around this atom = 358°). In the crystal, molecules are aggregated by two kinds of N—H...N hydrogen bonds into fusedR22(12) andR66(26) rings, forming a slightly puckered two-dimensional array lying parallel to (101).

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Khokhlov, Alexander L., Ilya I. Yaichkov, Mikhail A. Alexeev, et al. "Identification and synthesis of metabolites of the new 4.5-dihydroisoxazol-5-carboxamide derivate." Research Results in Pharmacology 10, no. 2 (2024): 83–95. http://dx.doi.org/10.18413/rrpharmacology.10.482.

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Introduction: 3-(2-butyl-5-chloro-1H-imidazole-4-yl)-N-[4-methoxy-3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazole-5-carboxamide is new antirheumatic drug. It is necessary to identify and synthesize the biotransformation products for its complete pharmacokinetic study. Materials and Methods: A biotransformation study was carried out by intraperitoneal administration of the drug to Wistar rats and Soviet Chinchilla breed rabbits. Animal blood sampling was performed before the injection and 0.5 h, 1 h, 2 h, 4 h, 24 h after the injection of the investigated compound. The samples were immediatel

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30

Mukhtorov, Loik G., Yevgenia V. Ivanova, Igor' V. Blokhin, et al. "SYNTHESIS AND STRUCTURE OF NEW DERIVATIVES OF 10-R-4-METHYL-1,8-DINITRO-3-OXA-5,10-DIAZATRICYCLO[6.3.1.02.6]DODECA-2(6),4-DIENE." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 63, no. 1 (2019): 4–10. http://dx.doi.org/10.6060/ivkkt.20206301.5944.

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The spatial and electronic structure of 2-methyl-5,7-dinitrobenzo[d]oxazole, which is the substrate for the synthesis of hydride σ-adducts, was studied by the DFT/B3LYP/aug-cc-pVDZ method. Analysis of the charges on the atoms showed that the largest positive NBO charge is concentrated on the carbon atom C2 of the oxazole ring, while the carbon atoms C4 and C6 annelated benzene nucleus have the highest Mulliken charges both in the gas phase and in water. Thus, it has been established that a rigid base, a methoxide ion, is attached to the carbon atom C2, which is a hard reaction center, and a re

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31

Islor, Arun M., Rajiv Yaradoni, B. Garudachari, Thomas Gerber, Eric Hosten, and Richard Betz. "3-(4-Chlorophenyl)-5-phenyl-4,5-dihydro-1,3-oxazole." Acta Crystallographica Section E Structure Reports Online 68, no. 11 (2012): o3215. http://dx.doi.org/10.1107/s1600536812043711.

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32

Lei, Dongwei, Huibin Yang, Bin Li, and Zhuo Kang. "2-(3-Methyl-2-nitrophenyl)-4,5-dihydro-1,3-oxazole." Acta Crystallographica Section E Structure Reports Online 65, no. 1 (2008): o54. http://dx.doi.org/10.1107/s1600536808040920.

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33

Zhang, Ling-Juan, Mei-Chen Xu, Jie Liu та Xian-Ming Zhang. "Tandem cycloaddition–decarboxylation of α-keto acid and isocyanide under oxidant-free conditions towards monosubstituted oxazoles". RSC Advances 6, № 77 (2016): 73450–53. http://dx.doi.org/10.1039/c6ra16031j.

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An efficient method, tandem [3 + 2] cycloaddition–decarboxylation of α-keto acid and isocyanide promoted by copper salt, has been developed for constructing monosubstituted oxazole. The elegant approach ingeniously avoids consuming excess oxidants.

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34

Venkatasubramanian H, Sarojkumar Sha, Hemalatha S, and Easwaramoorthy D. "Synthesis, characterization of new nicotinamide-oxazole analogs, and their antimicrobial activity." International Journal of Research in Pharmaceutical Sciences 11, no. 2 (2020): 2707–12. http://dx.doi.org/10.26452/ijrps.v11i2.2292.

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Identification of a novel antimicrobial molecule is vital to research due to contaminated agro related products and injurious pathogens. Especially candida albicans is most common infective fungi in the present world, that cause hospital-acquired infections. There is a medical and biological need for the discovery of novel antimicrobial drugs with high potent in nature. This effort involved the synthesis of scaffold molecule, in which Vitamin B3 and oxazole plays vital role as pharmacophore moiety, where 2-(Nicotinamido) oxazole-4-Carboxylic acid coupled from pyridine–3-carboxylic acid (Nicoti

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35

Merzhyievskyi, D. O., O. V. Shablykin, O. V. Shablykina, N. M. Shevchenko, and V. S. Brovarets. "Two-stage threecomponent synthesis of 6,11-diaza-1,5(2,5)-dioxazole- 3(1,2)-benzenecycloundecapha ne-14,54- dicarbonitrile." Reports of the National Academy of Sciences of Ukraine, no. 11 (2020): 71–77. http://dx.doi.org/10.15407/dopovidi2020.11.071.

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The possibilities of 2-amino-3,3-dichloroacrylonitrile (ADAN) used for the construction of macrocyclic structures such as cyclophanes with two oxazole fragments are investigated. For this purpose, bifunctional reagents were used in the classic ADAN transformation into 5-amino-4-cyanooxazoles (sequential treatment of ADAN with acyl chloride and a primary or secondary amine). As a result of the reaction of 2,2'‎-(1,2-phenylene)-diacetyl chloride with 2 eq of ADAN, a compound with two acrylonitrile fragments, 2,2' ‎- (1,2-phenylene)bis(N- (2,2-dichloro-1-cyanovinyl)acetamide), was obtained. In th

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36

Sydorenko, Ivan A., Marija V. Mishchenko, Serhii Yu Shtrygol’, et al. "The synthesis and the anticonvulsant activity screening of new 5-substituted 2-imino-4-thiazolidinone derivatives." Journal of Organic and Pharmaceutical Chemistry 20, no. 1(77) (2022): 12–20. http://dx.doi.org/10.24959/ophcj.22.248784.

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Aim. To synthesize 5-ene-4-thiazolidinones containing heterocyclic rings in the molecule as potential anticonvulsants, and screen their anticonvulsant activity on a model of pentylenetetrazole (PTZ) seizures.Results and discussion. A straightforward and convenient synthesis of novel 5-ene-derivatives of thiazol/oxazole-bearing 4-thiazolidinones as possible anticonvulsant agents was performed. Compounds were characterized using methods of spectral analysis (1H NMR and LC-MS). 5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde underwent the aminolysis on a chlorine atom by a molecule of monoe

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37

Nassiri, Mahmoud. "A novel, simple, and facile synthesis of 3-(3-benzyl-2,3-dihydrobenzo[d]thiazol-2-yl)benzo[d]oxazole-2(3H)-thione derivatives." Journal of Chemical Research 47, no. 2 (2023): 174751982311652. http://dx.doi.org/10.1177/17475198231165254.

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Novel 3-(3-benzyl-2,3-dihydrobenzo[ d]thiazol-2-yl)benzo[ d]oxazole-2(3 H)-thione derivatives are efficiently synthesized in excellent yields by reactions of benzothiazoles, benzyl bromides, and 2-mercaptobenzoxazole in acetone under catalyst-free conditions in the presence of triethylamine. The structures of the products are confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy, electron ionization mass spectrometry, and elemental analyses.

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38

Li, Gang, Li Li, Haihong Huang, and Dali Yin. "Ti(iv)-catalyzed cascade synthesis of tetrahydrofuro[3,2-d]oxazole from arene-1,4-diones." Organic & Biomolecular Chemistry 13, no. 15 (2015): 4418–21. http://dx.doi.org/10.1039/c5ob00174a.

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The tandem ionic hydrogenation, ketalization, and intramolecular cyclization of arene-1,4-diones with a combination of TiCl<sub>4</sub>/Et<sub>3</sub>SiH give facile access to tetrahydrofuro[3,2-d]oxazole derivatives in good yields at room temperature.

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39

Olczak, Andrzej, Jarosław Sukiennik, Beata Olszewska, Monika Stefaniak, Krzysztof Walczyński, and Małgorzata Szczesio. "Structures 4-n-propyl Piperazines as Non-Imidazole Histamine H3 Antagonists." Materials 14, no. 22 (2021): 7094. http://dx.doi.org/10.3390/ma14227094.

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Seven new low-temperature structures of 4-n-propylpiperazine derivatives, potential H3 receptor antagonists, have been determined by X-ray crystallography, with the following symmetry and unit cell parameters: 2-(4-propyl-piperazin-1-yl)oxazolo[4,5-c]pyridine (compound 1), P-1, 5.9496 Å, 12.4570 Å, 12.8656 Å, 112.445°, 95.687°, 103.040°; 2-(4-propyl-piperazin-1-yl)thia-zolo[4,5-c]pyridine (compound 2), I2/a, 22.2087 Å, 7.5519 Å, 19.9225 Å, β = 92.368°; 2-(4-propyl-piperazin-1-yl)oxazolo[5,4-c]pyridine (compound 3), C2/c, 51.1351 Å, 9.36026 Å, 7.19352 Å, β = 93.882°; 2-(4-propyl-piperazin-1-yl)

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OuYang, Yiqiang, Caolin Wang, Bingbing Zhao, et al. "Design, synthesis, antiproliferative activity and docking studies of quinazoline derivatives bearing oxazole or imidazole as potential EGFR inhibitors." New Journal of Chemistry 42, no. 21 (2018): 17203–15. http://dx.doi.org/10.1039/c8nj03594f.

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Six series of quinazoline derivatives bearing oxazole or imidazole (8a–f, 9a–f, 10a–d, 11a–f, 12a–d and 13a–i) were designed, synthesized and their IC<sub>50</sub> values evaluated against three cancer cell lines (A549, MCF-7 and PC-3).

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41

Vaarla, Krishnaiah, V. Rajeswar Rao, and Mehmet Akkurt. "Crystal structure of 3-benzylsulfanyl-6-(5-methyl-1,2-oxazol-3-yl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole." Acta Crystallographica Section E Crystallographic Communications 71, no. 11 (2015): o809—o810. http://dx.doi.org/10.1107/s2056989015017351.

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In the title compound, C14H11N5OS2, the triazolo–thiadiazole system is essentially planar (r.m.s. deviation = 0.002 Å) and makes dihedral angles of 6.33 (12) and 42.95 (14)° with the planes of the oxazole and phenyl rings, respectively. In the crystal, face-to-face π–π interactions are observed between the thiadiazole and oxazole rings [centroid–centroid distance = 3.4707 (18) Å], leading to columns along [010].

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42

Meundaeng, Natthaya, Timothy John Prior, and Apinpus Rujiwatra. "Crystal structures and Hirshfeld surface analysis of transition-metal complexes of 1,3-azolecarboxylic acids." Acta Crystallographica Section C Structural Chemistry 75, no. 9 (2019): 1319–26. http://dx.doi.org/10.1107/s2053229619011525.

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The crystal structures of five new transition-metal complexes synthesized using thiazole-2-carboxylic acid (2-Htza), imidazole-2-carboxylic acid (2-H2ima) or 1,3-oxazole-4-carboxylic acid (4-Hoxa), namely diaquabis(thiazole-2-carboxylato-κ2 N,O)cobalt(II), [Co(C4H2NO2S)2(H2O)2], 1, diaquabis(thiazole-2-carboxylato-κ2 N,O)nickel(II), [Ni(C4H2NO2S)2(H2O)2], 2, diaquabis(thiazole-2-carboxylato-κ2 N,O)cadmium(II), [Cd(C4H2NO2S)2(H2O)2], 3, diaquabis(1H-imidazole-2-carboxylato-κ2 N 3,O)cobalt(II), [Co(C4H2N2O2)2(H2O)2], 4, and diaquabis(1,3-oxazole-4-carboxylato-κ2 N,O 4)cobalt(II), [Co(C4H2NO3)2(H

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43

Murai, Kenichi, Yusuke Takahara, Tomoyo Matsushita, Hideyuki Komatsu, and Hiromichi Fujioka. "Facile Preparation of Oxazole-4-carboxylates and 4-Ketones from Aldehydes using 3-Oxazoline-4-carboxylates as Intermediates." Organic Letters 12, no. 15 (2010): 3456–59. http://dx.doi.org/10.1021/ol1012789.

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44

Varlow, Cassis, Andrew V. Mossine, Vadim Bernard-Gauthier, Peter J. H. Scott, and Neil Vasdev. "Radiofluorination of oxazole-carboxamides for preclinical PET neuroimaging of GSK-3." Journal of Fluorine Chemistry 245 (May 2021): 109760. http://dx.doi.org/10.1016/j.jfluchem.2021.109760.

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45

Volchkov, V. V., G. V. Dem’yanov, M. V. Rusalov, and T. I. Syreishchikova. "Fluorescence Depolarization Kinetics of Neutral and Charged 2-(3′-Pyridyl)oxazole." Russian Journal of General Chemistry 75, no. 5 (2005): 790–94. http://dx.doi.org/10.1007/s11176-005-0319-6.

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46

Marchand, Alan P., D. Rajagopal, and Simon G. Bott. "Rearrangements of substituted 3-azidoazetidines: Unexpected formation of a substituted oxazole." Journal of Heterocyclic Chemistry 32, no. 4 (1995): 1409–11. http://dx.doi.org/10.1002/jhet.5570320453.

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47

Barański, Andrzej, and Jerzy Cioslowski. "MNDO study of the [2 + 3] cycloaddition of nitroethene to formonitrile N-oxide." Collection of Czechoslovak Chemical Communications 56, no. 6 (1991): 1167–72. http://dx.doi.org/10.1135/cccc19911167.

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Two regioisomeric pathways have been studied by MNDO method for nitroethene [2 + 3] cycloaddition to formonitrile N-oxide. It has been found that four critical structures are located along each of the pathways. Calculations indicate that both reactions take place in a concerted manner and that their transition states are early. Moreover, it was established that the path leading to 5-nitro-4,5-dihydro-1,2-oxazole is preferred.

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48

Parab, R. H., and B. C. Dixit. "Synthesis, Characterization and Antimicrobial Activity of Imidazole Derivatives Based on 2-chloro-7-methyl-3-formylquinoline." E-Journal of Chemistry 9, no. 3 (2012): 1188–95. http://dx.doi.org/10.1155/2012/164235.

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A series of oxazole and thereof imidazole derivatives were prepared from 2-chloro-7-methyl-3-formyl quinoline. The structures of all synthesized compounds were elucidated by elemental, IR,1HNMR,13CNMR spectra. Supplementary to these, they were assayedin vitrofor their antimicrobial activity; it was revealed that some synthesized derivatives were exhibiting competent biological activity against both gram negative and gram positive bacterial species and fungal microorganisms.

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Karikalan, Kaviya. "Molecular docking analysis of the oral tumor target JAK STAT 3 with oxo-azo compounds." Bioinformation 19, no. 1 (2023): 63–68. http://dx.doi.org/10.6026/97320630019063.

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It is of interest to identify the JAK STAT 3 signaling inhibitors to abrogate tumorigenesis in oral cancer. Hence, molecular docking was performed with known oxazole compounds (1-5) and the 3D crystal structure of JAK-1 protein from Homo sapiens (PDB ID: 3EYG). The results show that the oxo-azo derivatives showed better interactions within the binding site of proteins. We report that compounds 1, 4 and 5 optimal binding features with JAK STAT 3.

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Jung, Hee Jin, Hyeon Seo Park, Hye Soo Park, et al. "Exploration of Compounds with 2-Phenylbenzo[d]oxazole Scaffold as Potential Skin-Lightening Agents through Inhibition of Melanin Biosynthesis and Tyrosinase Activity." Molecules 29, no. 17 (2024): 4162. http://dx.doi.org/10.3390/molecules29174162.

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Inspired by the potent tyrosinase inhibitory activity of phenolic compounds with a 2-phenylbenzo[d]thiazole scaffold, we explored phenolic compounds 1–15 with 2-phenylbenzo[d]oxazole, which is isosterically related to 2-phenylbenzo[d]thiazole, as novel tyrosinase inhibitors. Among these, compounds 3, 8, and 13, featuring a resorcinol structure, exhibited significantly stronger mushroom tyrosinase inhibition than kojic acid, with compound 3 showing a nanomolar IC50 value of 0.51 μM. These results suggest that resorcinol plays an important role in tyrosinase inhibition. Kinetic studies using Lin

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