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Journal articles on the topic '1,2,4-Oxadiazoles'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Puzanov, Andrey I., Dmitry S. Ryabukhin, Anna S. Zalivatskaya, et al. "Synthesis of 5-arylacetylenyl-1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions." Beilstein Journal of Organic Chemistry 17 (September 15, 2021): 2417–24. http://dx.doi.org/10.3762/bjoc.17.158.

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Acetylene derivatives of 1,2,4-oxadiazoles, i.e., 5-(2-arylethynyl)-3-aryl-1,2,4-oxadiazoles, have been obtained, for the first time reported, from 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles by their bromination at the carbon–carbon double bond followed by di-dehydrobromination with NaNH2 in liquid NH3. The reaction of the acetylenyl-1,2,4-oxadiazoles with arenes in neat triflic acid TfOH (CF3SO3H) at room temperature for 1 h resulted in the formation of E/Z-5-(2,2-diarylethenyl)-3-aryl-1,2,4-oxadiazoles as products of regioselective hydroarylation of the acetylene bond. The addition of TfOH t

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2

Ölmez, Nevin Arıkan, and Faryal Waseer. "New Potential Biologically Active Compounds: Synthesis and Characterization of Urea and Thiourea Derivativpes Bearing 1,2,4-oxadiazole Ring." Current Organic Synthesis 17, no. 7 (2020): 525–34. http://dx.doi.org/10.2174/1570179417666200417112106.

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Background: Urea, thiourea, and 1,2,4-oxadiazole compounds are of great interest due to their different activities such as anti-inflammatory, antiviral, analgesic, fungicidal, herbicidal, diuretic, antihelminthic and antitumor along with antimicrobial activities. Objective: In this work, we provide a new series of potential biologically active compounds containing both 1,2,4-oxadiazole and urea/thiouprea moiety. Materials and Methods: Firstly, 5-chloromethyl-3-aryl-1,2,4-oxadiazoles (3a-j) were synthesized from the reaction of different substituted amidoximes (2a-j) and chloroacetyl chloride i

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3

Zalivatskaya, Anna S., Dmitry S. Ryabukhin, Marina V. Tarasenko, et al. "Metal-free hydroarylation of the side chain carbon–carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid." Beilstein Journal of Organic Chemistry 13 (May 11, 2017): 883–94. http://dx.doi.org/10.3762/bjoc.13.89.

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The metal-free reaction of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles with arenes in neat triflic acid (TfOH, CF3SO3H), both under thermal and microwave conditions, leads to 5-(2,2-diarylethyl)-3-aryl-1,2,4-oxadiazoles. The products are formed through the regioselective hydroarylation of the side chain carbon–carbon double bond of the starting oxadiazoles in yields up to 97%. According to NMR data and DFT calculations, N4,C-diprotonated forms of oxadiazoles are the electrophilic intermediates in this reaction.

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4

Srivastava, Rajendra M. "Mass spectrometric analysis of 1,2,4-Oxadiazoles and 4,5-Dihydro-1,2,4-Oxadiazoles." Mass Spectrometry Reviews 24, no. 3 (2005): 328–46. http://dx.doi.org/10.1002/mas.20017.

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5

Torgova, S. I., T. A. Geivandova, O. Francescangeli, and A. Strigazzi. "Banana-shaped 1,2,4-oxadiazoles." Pramana 61, no. 2 (2003): 239–48. http://dx.doi.org/10.1007/bf02708306.

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6

MOURA, A. L., J. F. SILVA, J. J. R. DE FREITAS, J. C. R. FREITAS, and J. R. DE FREITAS FILHO. "EXPERIENCING A SYNTHESIS ONE-POT OF 1,2,4-OXADIAZOLE MEDIATED BY MICROWAVE OVEN: GREEN CHEMISTRY IN FOCUS." Periódico Tchê Química 16, no. 32 (2019): 820–32. http://dx.doi.org/10.52571/ptq.v16.n32.2019.838_periodico32_pgs_820_832.pdf.

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1,2,4-oxadiazoles are compounds that have attracted the attention of many researchers due to their wide range of biological activities, for example, anti-inflammatory, antimicrobial, antitumor etc. The syntheses are based mostly on the use of amidoximes and acylating agents as the initial reactants. This work aims to describe a one-pot reaction for the synthesis of 1,2,4-oxadiazols, mediated by microwave irradiation, employing home-use microwave oven, in the discipline of heterocyclic Chemistry in the postgraduate. The methodology consisted of the reaction of nitriles, hydroxylamine hydrochlor

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7

Vinaya, Kambappa, Ganganahalli K. Chandrashekara, and Prasanna D. Shivaramu. "One-pot synthesis of 3,5-diaryl substituted-1,2,4-oxadiazoles using gem-dibromomethylarenes." Canadian Journal of Chemistry 97, no. 9 (2019): 690–96. http://dx.doi.org/10.1139/cjc-2018-0333.

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1,2,4-Oxadiazole is one of the most promising heterocyclic ring systems in medicinal chemistry. In the present paper, we report the method for an efficient one-pot synthesis of 3,5-diaryl substituted 1,2,4-oxadiazoles using a two-component reaction of gem-dibromomethylarenes with amidoximes in good yields. In this method, gem-dibromomethylarenes are used as benzoic acid equivalents for the efficient synthesis of aryl-substituted 1,2,4-oxadiazoles. It is anticipated that this methodology will have versatile applications in the practical syntheses of various molecules of both medicinal and mater

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8

Capretz-Agy, André, Fábio S. Fernandes, Manoel T. Rodrigues, Caroline Conti, and Fernando Coelho. "Aza-Morita–Baylis–Hillman Reaction with Vinyl-oxadiazoles: An Expeditious Approach to Access New Heterocyclic Arrangements." Synlett 31, no. 06 (2019): 622–26. http://dx.doi.org/10.1055/s-0039-1691497.

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In this communication, we disclosed a new aza-MBH reaction in which traditional nucleophilic partners of these reactions (e.g., acrylates, nitroolefins or enones) were replaced by vinyl-1,2,4-oxadiazoles. Thus, the aza-MBH reaction between 5-aryl-3-vinyl-1,2,4-oxadiazoles and N-sulfonylimines, catalyzed by the mixture DABCO/AcOH, provides a class of new adduct in yields varying from 31% up to 93% in reaction times from 30 minutes to 24 hours. Due to the biological activities and technological applications associated with the 1,2,4-oxadiazole motifs, this new class of heterocycles offers great

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9

Heimann, Dominik, Corinna Lueg, Henk de Vries, et al. "Bioisosteric replacement of central 1,2,4-oxadiazole ring of high affinity CB2 ligands by regioisomeric 1,3,4-oxadiazole ring." MedChemComm 8, no. 8 (2017): 1697–705. http://dx.doi.org/10.1039/c7md00296c.

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Three pairs of regioisomeric 1,2,4- and 1,3,4-oxadiazoles were synthesized as selective CB<sub>2</sub> ligands. Although the 1,3,4-oxadiazoles should have better physicochemical and pharmacokinetic properties, their CB<sub>2</sub> affinity was reduced.

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10

Herath, Ananda, and Nicholas D. P. Cosford. "Continuous-flow synthesis of highly functionalized imidazo-oxadiazoles facilitated by microfluidic extraction." Beilstein Journal of Organic Chemistry 13 (February 7, 2017): 239–46. http://dx.doi.org/10.3762/bjoc.13.26.

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A versatile continuous-flow synthesis of highly functionalized 1,2,4-oxadiazoles starting from carboxylic acids is reported. This process was applied to the multistep synthesis of imidazo[1,2-a]pyridin-2-yl-1,2,4-oxadiazoles, using a three reactor, multistep continuous-flow system without isolation of intermediates. This continuous-flow method was successfully combined with a single-step liquid–liquid microextraction unit to remove high boiling point polar solvents and impurities and provides the target compounds in high purity with excellent overall yields.

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11

Yarovenko, V. N., V. K. Taralashvili, I. V. Zavarzin, and M. M. Krayushkin. "New synthesis of 1,2,4-oxadiazoles." Tetrahedron 46, no. 11 (1990): 3941–52. http://dx.doi.org/10.1016/s0040-4020(01)90529-0.

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12

Eloy, F., and A. Deryckere. "Synthèse D'Amino-3 Oxadiazoles-1,2,4." Bulletin des Sociétés Chimiques Belges 78, no. 1-2 (2010): 41–46. http://dx.doi.org/10.1002/bscb.19690780106.

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13

Darehkordi, Ali, Mahin Ramezani, and Fariba Rahmani. "TiO2 -Nanoparticles Catalyzed Synthesis of New Trifluoromethyl-4,5-dihydro-1,2,4-oxadiazoles and Trifluoromethyl-1,2,4-oxadiazoles." Journal of Heterocyclic Chemistry 55, no. 7 (2018): 1702–8. http://dx.doi.org/10.1002/jhet.3207.

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14

Sams, Christian K., and Jesper Lau. "Solid-phase synthesis of 1,2,4-oxadiazoles." Tetrahedron Letters 40, no. 52 (1999): 9359–62. http://dx.doi.org/10.1016/s0040-4039(99)01983-8.

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15

Pace, Andrea, and Paola Pierro. "The new era of 1,2,4-oxadiazoles." Organic & Biomolecular Chemistry 7, no. 21 (2009): 4337. http://dx.doi.org/10.1039/b908937c.

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16

Dürüst, Yaşar, Cevher Altuğ, and Ferdi Kiliç. "Thiophene-Substituted 1,2,4-Oxadiazoles and Oxadiazines." Phosphorus, Sulfur, and Silicon and the Related Elements 182, no. 2 (2007): 299–313. http://dx.doi.org/10.1080/10426500600919124.

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17

Pipik, Brenda, Guo‐Jie Ho, J. Michael Williams, and David A. Conlon. "A Preferred Synthesis of 1,2,4‐Oxadiazoles." Synthetic Communications 34, no. 10 (2004): 1863–70. http://dx.doi.org/10.1081/scc-120034169.

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18

Kayukova, L. A. "Synthesis of 1,2,4-oxadiazoles (a review)." Pharmaceutical Chemistry Journal 39, no. 10 (2005): 539–47. http://dx.doi.org/10.1007/s11094-006-0017-7.

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19

Karamysheva, Ludmila A., Irina F. Agafonova, Sofia I. Torgova, Boris A. Umanskii, and Alfredo Strigazzi. "Liquid Crystalline Pyridine Containing 1,2,4-Oxadiazoles." Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals 364, no. 1 (2001): 547–56. http://dx.doi.org/10.1080/10587250108025024.

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20

Cunha, Felipe S., and Alcino P. de Aguiar. "Synthesis and Bioactivity of 1,2,4-Oxadiazoles." Revista Virtual de Química 7, no. 6 (2015): 2509–30. http://dx.doi.org/10.5935/1984-6835.20150150.

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21

Tarasenko, M. V., E. R. Kofanov, S. V. Baikov, G. G. Krasovskaya, and A. S. Danilova. "Selective reduction of 5-alkenyl-3-(nitrophenyl)-1,2,4-oxadiazoles to 5-alkenyl-3-(aminophenyl)-1,2,4-oxadiazoles." Russian Journal of Organic Chemistry 53, no. 7 (2017): 1085–89. http://dx.doi.org/10.1134/s1070428017070211.

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22

Nandeesh, Kebballi N., Hassan A. Swarup, Nagarakere C. Sandhya, et al. "Synthesis and antiproliferative efficiency of novel bis(imidazol-1-yl)vinyl-1,2,4-oxadiazoles." New Journal of Chemistry 40, no. 3 (2016): 2823–28. http://dx.doi.org/10.1039/c5nj02925b.

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23

Guo, Wei, Kunbo Huang, Fanghua Ji, Wanqing Wu, and Huanfeng Jiang. "A facile approach to synthesize 3,5-disubstituted-1,2,4-oxadiazoles via copper-catalyzed-cascade annulation of amidines and methylarenes." Chemical Communications 51, no. 42 (2015): 8857–60. http://dx.doi.org/10.1039/c5cc02110c.

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A tandem Cu-catalyzed oxidation–amination–cyclization reaction for synthesizing various 3,5-disubstituted-1,2,4-oxadiazoles from easily available amidines and methylarenes or methylhetarenes is reported.

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24

Grambal, František, and Jan Lasovský. "Cyclization and acid-catalyzed hydrolysis of O-benzoylbenzamidoximes." Collection of Czechoslovak Chemical Communications 51, no. 12 (1986): 2786–97. http://dx.doi.org/10.1135/cccc19862786.

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Kinetics of formation of 1,2,4-oxadiazoles from 24 substitution derivatives of O-benzoylbenzamidoxime have been studied in sulphuric acid and aqueous ethanol media. It has been found that this medium requires introduction of the Hammett H0 function instead of the pH scale beginning as low as from 0.1% solutions of mineral acids. Effects of the acid concentration, ionic strength, and temperature on the reaction rate and on the kinetic isotope effect have been followed. From these dependences and from polar effects of substituents it was concluded that along with the cyclization to 1,2,4-oxadiaz

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25

Gupta, Puneet K., Mohd Kamil Hussain, Mohd Asad, et al. "A metal-free tandem approach to prepare structurally diverse N-heterocycles: synthesis of 1,2,4-oxadiazoles and pyrimidinones." New J. Chem. 38, no. 7 (2014): 3062–70. http://dx.doi.org/10.1039/c4nj00361f.

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N-heterocycles, namely 1,2,4-oxadiazoles and 2,6 disubstituted pyrimidin-4-ones, have been synthesised in one pot via carboxamidation of amidines with aryl carboxylic acids and aryl propargylic acids under metal-free conditions.

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26

Smirnov, Andrey S., Ekaterina S. Yandanova, Nadezhda A. Bokach, et al. "Zinc(ii)-mediated generation of 5-amino substituted 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and O2-involving transformations." New Journal of Chemistry 39, no. 12 (2015): 9330–44. http://dx.doi.org/10.1039/c5nj02061a.

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27

Mitchell, William R., and R. Michael Paton. "Thermal fragmentation of 1,2,5- and 1,2,4-oxadiazoles." Arkivoc 2009, no. 14 (2010): 200–216. http://dx.doi.org/10.3998/ark.5550190.0010.e19.

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28

Tolmachev, Andrey, Andrey V. Bogolubsky, Sergey E. Pipko, et al. "Expanding Synthesizable Space of Disubstituted 1,2,4-Oxadiazoles." ACS Combinatorial Science 18, no. 10 (2016): 616–24. http://dx.doi.org/10.1021/acscombsci.6b00103.

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29

Nishiwaki, Nagatoshi, Masahiro Ariga, Mina Tamura, Yumiko Ise, and Yoshikazu Okajima. "Facile Synthesis of 3-Carbamoyl-1,2,4-Oxadiazoles." Synthesis 2006, no. 20 (2006): 3453–61. http://dx.doi.org/10.1055/s-2006-950210.

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30

Palumbo Piccionello, Antonio, Andrea Pace, and Silvestre Buscemi. "Tandem Reactions of 1,2,4-Oxadiazoles with Allylamines." Organic Letters 13, no. 17 (2011): 4749–51. http://dx.doi.org/10.1021/ol201676g.

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31

Wang, Zuoquan, Hong Zhang, Farukh Jabeen, et al. "Synthesis and Properties of Energetic 1,2,4-Oxadiazoles." European Journal of Organic Chemistry 2015, no. 34 (2015): 7468–74. http://dx.doi.org/10.1002/ejoc.201501056.

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32

dos Anjos, Janaína V., Denis Sinou, Sebastiao J. de Melo, and Rajendra M. Srivastava. "Synthesis of glycosyl-triazole linked 1,2,4-oxadiazoles." Carbohydrate Research 342, no. 16 (2007): 2440–49. http://dx.doi.org/10.1016/j.carres.2007.07.011.

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33

Korotkikh, N. I., A. V. Kiselev, A. V. Knishevitsky, G. F. Raenko, T. M. Pekhtereva, and O. P. Shvaika. "Recyclization of 1,3,4-Oxadiazoles and Bis-1,3,4-oxadiazoles into 1,2,4-Triazole Derivatives. Synthesis of 5-Unsubstituted 1,2,4-Triazoles." Chemistry of Heterocyclic Compounds 41, no. 7 (2005): 866–71. http://dx.doi.org/10.1007/s10593-005-0240-2.

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34

Kayukova, Lyudmila, Anna Vologzhanina, Kaldybai Praliyev, et al. "Boulton-Katritzky Rearrangement of 5-Substituted Phenyl-3-[2-(morpholin-1-yl)ethyl]-1,2,4-oxadiazoles as a Synthetic Path to Spiropyrazoline Benzoates and Chloride with Antitubercular Properties." Molecules 26, no. 4 (2021): 967. http://dx.doi.org/10.3390/molecules26040967.

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The analysis of stability of biologically active compounds requires an accurate determination of their structure. We have found that 5-aryl-3-(2-aminoethyl)-1,2,4-oxadiazoles are generally unstable in the presence of acids and bases and are rearranged into the salts of spiropyrazolinium compounds. Hence, there is a significant probability that it is the rearranged products that should be attributed to biological activity and not the primarily screened 5-aryl-3-(2-aminoethyl)-1,2,4-oxadiazoles. A series of the 2-amino-8-oxa-1,5-diazaspiro[4.5]dec-1-en-5-ium (spiropyrazoline) benzoates and chlor

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35

Donnier-Maréchal, Marion, David Goyard, Vincent Folliard, et al. "3-Glucosylated 5-amino-1,2,4-oxadiazoles: synthesis and evaluation as glycogen phosphorylase inhibitors." Beilstein Journal of Organic Chemistry 11 (April 17, 2015): 499–503. http://dx.doi.org/10.3762/bjoc.11.56.

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Glycogen phosporylase (GP) is a promising target for the control of glycaemia. The design of inhibitors binding at the catalytic site has been accomplished through various families of glucose-based derivatives such as oxadiazoles. Further elaboration of the oxadiazole aromatic aglycon moiety is now reported with 3-glucosyl-5-amino-1,2,4-oxadiazoles synthesized by condensation of a C-glucosyl amidoxime with N,N’-dialkylcarbodiimides or Vilsmeier salts. The 5-amino group introduced on the oxadiazole scaffold was expected to provide better inhibition of GP through potential additional interaction

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36

Palumbo Piccionello, Antonio, Annalisa Guarcello, Silvestre Buscemi, Nicolò Vivona, and Andrea Pace. "Synthesis of Amino-1,2,4-triazoles by Reductive ANRORC Rearrangements of 1,2,4-Oxadiazoles." Journal of Organic Chemistry 75, no. 24 (2010): 8724–27. http://dx.doi.org/10.1021/jo102049r.

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37

SUI Yan, 隋岩, 郭剑 GUO Jian, 曹建华 CAO Jian-hua, and 华瑞茂 HUA Rui-mao. "Synthesis of novel 1,2,4-oxadiazoles liquid crystalline compounds." Chinese Journal of Liquid Crystals and Displays 29, no. 1 (2014): 1–6. http://dx.doi.org/10.3788/yjyxs20142901.0001b.

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38

Kivrak, Arif, and Metin Zora. "A novel synthesis of 1,2,4-oxadiazoles and isoxazoles." Tetrahedron 70, no. 4 (2014): 817–31. http://dx.doi.org/10.1016/j.tet.2013.12.043.

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39

Deegan, Tracy L., Theodore J. Nitz, Diane Cebzanov, Denise E. Pufko, and John A. Porco. "Parallel synthesis of 1,2,4-oxadiazoles using CDI activation." Bioorganic & Medicinal Chemistry Letters 9, no. 2 (1999): 209–12. http://dx.doi.org/10.1016/s0960-894x(98)00712-4.

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40

Molina, P., M. Alajarin, and A. Ferao. "Iminophosphorane-Mediated Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles." Synthesis 1986, no. 10 (1986): 843–45. http://dx.doi.org/10.1055/s-1986-31799.

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41

Mironov, Maxim E., Mikhail A. Pokrovsky, Yurii V. Kharitonov, Makhmut M. Shakirov, Andrey G. Pokrovsky, and Elvira E. Shults. "Furanolabdanoid-based 1,2,4-oxadiazoles: Synthesis and cytotoxic activity." ChemistrySelect 1, no. 3 (2016): 417–24. http://dx.doi.org/10.1002/slct.201600042.

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42

BUZYKIN, B. I., and O. A. KHARITONOVA. "ChemInform Abstract: A New Way to 1,2,4-Oxadiazoles." ChemInform 25, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199441135.

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43

Humphrey, Guy R., and Stanley H. B. Wright. "A novel synthesis of 3-bromo-1,2,4-oxadiazoles." Journal of Heterocyclic Chemistry 26, no. 1 (1989): 23–24. http://dx.doi.org/10.1002/jhet.5570260105.

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44

Torgova, Sofia I., Ludmila A. Karamysheva, Tatiana A. Geivandova, and Alfredo Strigazzi. "Banana-Shaped 1,2,4-Oxadiazole Analogues of 1,3,4-Oxadiazoles." Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals 365, no. 1 (2001): 99–106. http://dx.doi.org/10.1080/10587250108025286.

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45

YASUMOTO, Masahiko, Kohshin YANAGIYA, Isao SHIBUYA, and Midori GOTO. "The synthesis of 1,2,4-oxadiazoles under high pressure." NIPPON KAGAKU KAISHI, no. 10 (1987): 1807–12. http://dx.doi.org/10.1246/nikkashi.1987.1807.

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46

Thottempudi, Venugopal, Jiaheng Zhang, Chunlin He, and Jean'ne M. Shreeve. "Azo substituted 1,2,4-oxadiazoles as insensitive energetic materials." RSC Adv. 4, no. 92 (2014): 50361–64. http://dx.doi.org/10.1039/c4ra10821c.

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47

Massacesi, Marcella, Gerolamo Devoto, and Gioanna Gelli. "Metal complexes with some 3-aryl-1,2,4-oxadiazoles." Spectrochimica Acta Part A: Molecular Spectroscopy 41, no. 12 (1985): 1433–36. http://dx.doi.org/10.1016/0584-8539(85)80199-9.

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48

Santagada, Vincenzo, Francesco Frecentese, Elisa Perissutti, Donatella Cirillo, Sara Terracciano, and Giuseppe Caliendo. "A suitable 1,2,4-oxadiazoles synthesis by microwave irradiation." Bioorganic & Medicinal Chemistry Letters 14, no. 17 (2004): 4491–93. http://dx.doi.org/10.1016/j.bmcl.2004.06.048.

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49

Trifonov, Rostislav E, Anna P Volovodenko, Sergei N Vergizov, et al. "Basicity of Phenyl- and Methyl-Substituted 1,2,4-Oxadiazoles." Helvetica Chimica Acta 88, no. 7 (2005): 1790–97. http://dx.doi.org/10.1002/hlca.200590140.

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50

Biernacki, Karol, Mateusz Daśko, Olga Ciupak, Konrad Kubiński, Janusz Rachon, and Sebastian Demkowicz. "Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery." Pharmaceuticals 13, no. 6 (2020): 111. http://dx.doi.org/10.3390/ph13060111.

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Five-membered 1,2,4-oxadiazole heterocyclic ring has received considerable attention because of its unique bioisosteric properties and an unusually wide spectrum of biological activities. Thus, it is a perfect framework for the novel drug development. After a century since the 1,2,4-oxadiazole have been discovered, the uncommon potential attracted medicinal chemists’ attention, leading to the discovery of a few presently accessible drugs containing 1,2,4-oxadiazole unit. It is worth noting that the interest in a 1,2,4-oxadiazoles’ biological application has been doubled in the last fifteen yea

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