Strategies for the Synthesis of [1,2,4]Triazolo[1,5-a]pyridine-8-carbonitriles

dc.citation.epage303
dc.citation.issue2
dc.citation.spage294
dc.contributor.affiliationTaras Shevchenko National University of Kyiv
dc.contributor.authorKhomenko, Dmytro
dc.contributor.authorShokol, Tetyana
dc.contributor.authorDoroshchuk, Roman
dc.contributor.authorRaspertova, Ilona
dc.contributor.authorLampeka, Rostyslav
dc.contributor.authorVolovenko, Yulian
dc.coverage.placenameЛьвів
dc.coverage.placenameLviv
dc.date.accessioned2024-02-12T08:30:45Z
dc.date.available2024-02-12T08:30:45Z
dc.date.created2023-03-16
dc.date.issued2023-03-16
dc.description.abstractКонденсовані гетероциклічні сполуки, що містять 1,2,4-триазольний цикл, становлять інтерес для науковців у зв’язку з їхнім широким застосуванням як у синтетичній, так і в медичній хімії. У цьому огляді вичерпно узагальнено методи синтезу [1,2,4]триазоло[1,5-a]піридин-8-карбонітрилів та класифіковано за типами використовуваних реагентів: перетворення 8-заміщених [1,2,4]триазоло[1,5-a]піридинів; синтези на основі функціоналізованих піридинів, що містять нітрильну групу; синтези на основі гетероциклізації 2-(1,2,4-триазол-5-іл) ацетонітрилів, ураховуючи циклоконденсації 2-(1,2,4-триазол-5-іл) ацетонітрилів з β-дикарбонільними сполуками та гетероциклізації 2-(1,2,4-триазол-5-іл)ацетонітрилів з α,β-ненасиченими нітрилами та естерами; циклоконденсації ациклічних реагентів, а саме похідних гідразину та заміщених метиленмалононітрилів або їхніх прекурсорів і рециклізацію солей оксадіазолопіридинію під дією аміаку або амінів.
dc.description.abstractConjugated heterocyclic compounds with a 1,2,4-triazole core are of scientific interest due to their wide application in both synthetic and medicinal chemistry. In this review, we comprehensively summarize the synthetic methods for [1,2,4]triazolo[1,5-a]pyridine-8-carbonitriles. The methods are classified as follows: convertion of 8-substituted [1,2,4]triazolo[1,5-a]pyridines; synthesis based on functionalized pyridines, containing a nitrile group; synthesis based on heterocyclization of 2-(1,2,4-triazol-5-yl) acetonitriles, including cyclocondensation of 2-(1,2,4-triazol-5-yl)acetonitriles with β-dicarbonyl compounds and heterocyclization of 2-(1,2,4-triazol-5-yl) acetonitriles with α,β-unsaturated nitriles and esters; cyclocondensation of acyclic reagents, namely hydrazine derivatives and substituted methylenemalononitriles or their precursors and recyclization of oxadiazolopyridinium salts upon the interaction with ammonia or amine.
dc.format.extent294-303
dc.format.pages10
dc.identifier.citationStrategies for the Synthesis of [1,2,4]Triazolo[1,5-a]pyridine-8-carbonitriles / Dmytro Khomenko, Tetyana Shokol, Roman Doroshchuk, Ilona Raspertova, Rostyslav Lampeka, Yulian Volovenko // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2023. — Vol 17. — No 2. — P. 294–303.
dc.identifier.citationenStrategies for the Synthesis of [1,2,4]Triazolo[1,5-a]pyridine-8-carbonitriles / Dmytro Khomenko, Tetyana Shokol, Roman Doroshchuk, Ilona Raspertova, Rostyslav Lampeka, Yulian Volovenko // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2023. — Vol 17. — No 2. — P. 294–303.
dc.identifier.doidoi.org/10.23939/chcht17.02.294
dc.identifier.issn1996-4196
dc.identifier.urihttps://ena.lpnu.ua/handle/ntb/61258
dc.language.isoen
dc.publisherВидавництво Львівської політехніки
dc.publisherLviv Politechnic Publishing House
dc.relation.ispartofChemistry & Chemical Technology, 2 (17), 2023
dc.relation.references[1] Mulwad, V.V.; Pawar, R.B. Synthesis of Biologically Active 5-Benzopyranylpyridines and Triazolopyridines. Indian J. Chem. Sect. B 2003, 42, 2901-2904. http://nopr.niscpr.res.in/handle/123456789/21765
dc.relation.references[2] Abudusaimi, M.Ye.F.; Sun, J.; Miyamoto, H.; Cheng, J-F.; Oka, D. Quinolone Compound. WO 2013029548, March 7, 2013.
dc.relation.references[3] Bassyouni, F.A.; Tawfik, H.A.; Hamed, A.R.; Soltan, M.M.; ElHefnawi, M.; ElRashedy, A.A.; Moharam, M.E.; Rehim, M.A. Synthesis, Antioxidant, and Antimicrobial Activities of New 2-(1,5,6-Trimethyl-1H-benzo[d]imidazole-2-carbonyl)-2,3-dihydro-1H-pyrazole-4-carbonitriles, (1,3,4-Oxadiazol-2-yl)-1H-benzo[d]-imidazol-5-yl)(phenyl)methanones, and (1,3,4-Oxadiazol-2-yl)-1,5-dihydro-[1,2,4]triazolo[1,5-a]pyridine-8-carbonitriles: QSAR and Molecular Docking Analysis. Egypt Pharm. J. 2012, 11, 80-92.
dc.relation.references[4] Azzam, R.A.; Elgemeie, G.H. Synthesis and Antimicrobial Evaluation of Novel N-Substituted 4-Ethylsulfanyl-2-pyridones and Triazolopyridines. Med Chem Res. 2019, 28, 62–70. https://doi.org/10.1007/s00044-018-2264-z
dc.relation.references[5] El-Adasy, A.A.; Hussein, A.M.; Ishak, E.A.; Hafiz, I.S.A.; Gawish, E.H.; Elapasery, M.A.; El-Gaby, M.S.A. Synthesis and Biological Evaluation of New 1,2,4-Triazolo[1,5-a] pyridine and 1,2,4-Triazolo[1,5-a] isoquinoline Derivatives Bearing Diphenyl Sulfide Moiety as Antimicrobial Agents. Egypt. J. Chem. 2021, 64, 913-921.
dc.relation.references[6] Kuroyanagi, J-I.; Kanai, K.; Sugimoto, Y.; Fujisawa, T.; Morita, C.; Suzuki, T.; Kawakami, K.; Takemura, M. Novel Antifungal Agents: Triazolopyridines as Inhibitors of β-1,6-Glucan Synthesis. Bioorg. Med. Chem. 2010, 18, 5845-5854. https://doi.org/10.1016/j.bmc.2010.06.096
dc.relation.references[7] Kawakaki, K.; Kanai, K.; Fujisawa, T.; Morita, C.; Suzuki, T. Fungicidal Heterocyclic Compounds. EP 1717238, November 2, 2006.
dc.relation.references[8] Mekheimer, R.A.; Sayed, A.A.R.; Ahmed, E.A. Novel 1,2,4-Triazolo[1,5-a]pyridines and Their Fused Ring Systems Attenuate Oxidative Stress and Prolong Lifespan of Caenorhabiditis elegans. J. Med. Chem. 2012, 55, 4169-4177. https://doi.org/10.1021/jm2014315
dc.relation.references[9] Mekheimer, R.A.; Sayed, A.A.R.; Ahmed, E.A.; Sadek, K.U. Synthesis and Characterization of New 1,2,4-Triazolo[1,5-a]-pyridines That Extend the Life Span of Caenorhabiditis elegans via Their Anti-Inflammatory/Antioxidant Effects. Arch. Pharm. Chem. Life Sci. 2015, 348, 650-665. https://doi.org/10.1002/ardp.201500069
dc.relation.references[10] Ismail, M.M.F.; Khalifa, N.M.; Fahmy, H.H.; EL-Sahrawy, H.M.; Nossier, E.S. Anticancer Evaluation of Novel 1,3,4-Trisubstituted Pyrazole Candidates Bearing Different Nitrogenous Heterocyclic Moieties. Biomedical Research 2016, 27, 1087-1093.
dc.relation.references[11] Flohr, A.; Groebke Zbinden, K.; Kuhn, B.; Lerne, C.; Rudolph, M.; Schaffhauser, H. Triazolo Compounds as PDE10 Inhibitors. WO 2013178572, December 5, 2013.
dc.relation.references[12] Wu, L.; Shen, B.; Li, J.; Li, Z.; Liu, K.; Zhang, F.; Yao, W. Heterocyclic Compounds as Immunomodulators. WO 2017070089, April 27, 2017.
dc.relation.references[13] Emmitte, K.A.; Lindsley, C.W.; Conn, P.J.; Felts, A.S.; Rodri-guez, A.L.; Smith, K.A.; Jones, C.K. Substituted Imidazopyridine and Triazolopyridine Compounds as Negative Allosteric Modula-tors of mGluR5. US 99844542, December 19, 2017.
dc.relation.references[14] Felt, A.S.; Rodriguez, A.L.; Morrison, R.D.; Bollinger, K.A.; Venable, D.F.; Blobaum, A.L.; Byers, F.W.; Thompson Gray, A.; Daniels, J.S.; Niswender, C.M.; et al. Discovery of Imidazo[1,2-a]-, [1,2,4]Triazolo[4,3-a]-, and [1,2,4]Triazolo[1,5-a]pyridine-8-carboxamide Negative Allosteric Modulators of Metabotropic Glutamatereceptor Subtype 5. Bioorganic Med. Chem. Lett. 2017, 27, 4858-4866. https://doi.org/10.1016/j.bmcl.2017.09.042
dc.relation.references[15] He, Z.; Zhang, J.; Guo, Y.; Fang, F.; Lu, J.; Cao, L.; Hu, H.; Li, X.; Xu, K. Triaryl[1,2,4]triazole[1,5-a]pyridine Derivate and Preparation Method Thereof. CN 106543175, March 29, 2017.
dc.relation.references[16] Lv, J.; He, Z.; Zhang, J.; Guo. Y.; Han. Z.; Bao, X. One-pot Synthesis of [1, 2, 4] Triazolo[1,5-a]pyridines from Azines and Benzylidenemalononitriles via Copper-Catalyzed Tandem Cycliza-tion. Tetrahedron 2018, 74, 3996-4004. https://doi.org/10.1016/j.tet.2018.06.002
dc.relation.references[17] Jones, G.; Sliskovic D.R. The Chemistry of the Triazolopyri-dines. Chem. Inf.-Dienst 1983, 34, 79-143. https://doi.org/10.1002/Chin.198420363
dc.relation.references[18] Jones, G. The Chemistry of the Triazolopyridines: An Update. Adv. Heterocycl. Chem. 2002, 100, 1-70. https://doi.org/10.1016/S0065-2725(02)83003-3
dc.relation.references[19] Vorobyov, A.Yu. Methods of Synthesis of [1,2,4]Triazolo[1,5-а]pyridines (Microreview). Chem. Heterocycl. Compd. 2019, 55, 695-697. https://doi.org/10.1007/s10593-019-02522-5
dc.relation.references[20] Vercek, B.; Leban, I.; Stanovnik, B.; Tisler, M. Neighboring group Interaction in ortho-Substituted Heterocycles. 2. 1,2,4-Oxadiazolylpyridines and Pyrido[2, 3-d]pyrimidine 3-Oxides. J. Org. Chem. 1979, 44, 1695-1699. https://doi.org/10.1021/jo01324a024
dc.relation.references[21] Phadke, R.C.; Rangnekar, D.W. A Novel, One-Step Synthesis of [1,2,4]Triazolo[1,5-a]pyridine Derivatives. Synthesis 1986, 10, 860-862. https://doi.org/10.1055/s-1986-31808
dc.relation.references[22] Ibrahim, M.A.; El-Gohary, N.M. Heterocyclization with Some Heterocyclic Diamines: Synthetic Approaches for Nitrogen Bridge-head Heterocyclic Systems. HeteroCycles 2014, 89, 1125-1157. https://doi.org/10.3987/REV-13-790
dc.relation.references[23] Khalifa, N.M.; Abdel-Rahman, A.A-H.; Abd-Elmoez, S.I.; Fathalla, O.A.; Abd El-Gwaad, A.A. A Convenient Synthesis of Some New Fused Pyridine and Pyrimidine Derivatives of Antim-icrobial Profiles. Res Chem Intermed. 2015, 41, 2295-2305. https://doi.org/10.1007/s11164-013-1347-1
dc.relation.references[24] Suresh, M.; Lavanya, P.; Rao, C.V. Synthesis and Pharmacological Evaluation of Novel 2H/6H-Thiazolo-[3’,2’:2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile Derivatives. Arabian J. Chem. 2016, 9, 136-142. https://doi.org/10.1016/j.arabjc.2011.02.004
dc.relation.references[25] Callejo, M.J.; Lafuente, P.; Martin-Leon, N.; Quinteiro, M.; Seoane, C.; Soto, J.L. A Convenient Preparation of [1,2,4]Triazolo[l,5-a]pyridines from Acetohydrazide Derivatives. Synthetic and Mechanistic Aspects. J. Chem. Soc., Perkin Trans. I. 1990, 1687-1690. https://doi.org/10.1039/P19900001687
dc.relation.references[26] Ibrahim, H.M.; Behbehani, H.; Arafa, W.A.A. A Facile, Practical and Metal-Free Microwave Assisted Protocol for mono- and bis-[1,2,4]Triazolo[1,5-a]pyridines Synthesis Utilizing 1-Amino-2-imino-pyridine Derivatives as Versatile Precursors. RSC Adv. 2020, 10, 15554-15572. https://doi.org/10.1039/D0RA02256J
dc.relation.references[27] Kockritz, P.; Riemer, B.; Michler, A.; Hassoun, A.; Liebscher, J. Synthesis of Pyrazolo[1,5-a]pyridines and Pyrazolo[1,5-c]pyrimidines by Reaction of Heterocyclic Amidrazones with 1,3-Dicarbonyl Compounds. J. Heterocycl. Chem. 1994, 31, 1157-1160. https://doi.org/10.1002/jhet.5570310510
dc.relation.references[28] Patzel, M.; Liebscher, J. Synthesis of Heterocycles by Reaction of Semicyclic 2-Aza-3-methylthio-propeniminium Salts with 1,4- and 1,5-Binucleophiles. J. Prakt. Chem. 1991, 333, 149-151. https://doi.org/10.1002/prac.19913330138
dc.relation.references[29] Behbehani, H.; Ibrahim, H.M. Pyrido[1,2-b]indazole Deriva-tives through AcOH and O2-Promoted Cross-dehydrogenative Coupling Reactions between 1,3-Dicarbonyl Compounds and N-Amino-2-iminopyridines. ACS Omega 2019, 4, 15289-15303. https://doi.org/10.1021/acsomega.9b02430
dc.relation.references[30] Khomenko, D.M.; Shokol, T.V.; Doroshchuk, R.O.; Starova, V.S.; Raspertova, I.V.; Shova, S.; Lampeka, R.D.; Volovenko, Yu.M. An Alternative Approach to the Synthesis of [1,2,4]Triazolo[1,5-a]-pyridine-8-carbonitriles, their Crystal Struc-ture and DFT Calculations. J. Het.Chem. 2021, 58, 1278-1285. https://doi.org/10.1002/jhet.4256
dc.relation.references[31] Chuiguk, V.A.; Fedotov, K.V. Formation of Condensed Pyridinium Cycles in the Reaction of Protonized Cyano- and Nitromethylazoles with 1,3-Diketones. Ukr. Khim. Zh. 1980, 46, 1306-1310.
dc.relation.references[32] Volovenko, Y.M.; Shokol, T.V. Convenient Method for the Annelation of a Pyridine Ring to Azaheterocyclic Systems. Chem. Heterocycl. Compd. 2003, 39, 545-546. https://doi.org/10.1023/A:1024738018872
dc.relation.references[33] Trottmann, G.H.; Hunkeler, W.; Jakob-Roetne, R.; Kilpatrick, G.J.; Nettekoven, M.H.; Riemer, C., inventor; Hoffmann-La Roche Inc., assignee. Amino-triazolopyridine Derivatives. US 6355653, March 12, 2002.
dc.relation.references[34] Milokhov, D.S.; Khilya, O.V.; Turov, A.V.; Medviediev, V.V.; Shishkin, O.V.; Volovenko, Yu.M. Hydroxypropyl Substituted Nitrogen Bridgehead Fused Cyanopyridines. Tetrahedron 2014, 70, 1214-1222. https://doi.org/10.1016/j.tet.2013.12.074
dc.relation.references[35] Zribi, L.; Zribi, F.; Marco-Contelles, J.; Chabchoub, F.; Ismaili, L. Facile One-Pot Synthesis of New [1,2,4]Triazolo[1,5-a]pyridine Derivatives by Ultrasonic Irradiation. Synth. Commun. 2017, 47, 1934-1939. https://doi.org/10.1080/00397911.2017.1357078
dc.relation.references[36] Martin, N.; Quinteiro, M.; Seoane, C.; Soto, J.L.; Fonseca, I.; Florencio, F.; Sanz, J. Two Rings in One Step: A Novel 1,2,4-Triazolo[1,5-a]pyridone with an Unusual Crystal Structure. J. Org. Chem. 1990, 55, 2259-2262. https://doi.org/10.1021/jo00294a058
dc.relation.references[37] Hadi, A.; Martin, N.; Seoane, C.; Soto, J.L.; Albert, A.; Cano, F. Synthesis and Crystal Structure of Piperidinium 2-Aryl[1,2,4]triazolo[1,5-a]pyridinides and their Neutralization to 2-Aryl[1,2,4]triazolo[1,5-a]-pyridines. J. Heterocycl. Chem. 1992, 29, 1229-1235. https://doi.org/10.1002/jhet.5570290531
dc.relation.references[38] Hadi, A. Synthesis of Novel [1,2,4]Triazolo[1,5-a]pyridines via Concerted Reactions Between 2-Cinnamoyl-2-cyanoacetohydrazide and α-Cyanocinamonitriles. J. Kerbala Univ. 2011, 9, 55-75.
dc.relation.references[39] Yamazaki, C.; Miyamoto, Y.; Sakima, H. Cyclization of Isothiosemicarbazones. Part 10. A Novel Route to 2-Amino[1,2,4]triazolo[1,5-a]pyridine Derivatives. J. Chem. Soc., Perkin Trans. 1 1994, 825-828. https://doi.org/10.1039/P19940000825
dc.relation.references[40] Alizadeh, A.; Saberi, V.; Mokhtari, J. A Simple One-Pot Procedure for the Synthesis of 1,2,4-Triazolo[1,5-a]pyridines via Pseudo Five-Component Reactions Catalyzed by Molecular Iodine. Synlett 2013, 24, 1825-1829. https://doi.org/10.1055/s-0033-1339333
dc.relation.references[41] Boyd, G.V.; Summers, A.J.H. The Action of Amines on I ,3,4-Oxadiazolium Salts. J. Chem. Soc. C. 1971, 409-414. https://doi.org/10.1039/J39710000409
dc.relation.references[42] Boyd, G.V.; Dando, S.R. The Action of Cyanamide on 1,3,4-Oxadiazolium and Pyrylium Salts. J. Chem. Soc. C. 1971, 3873-3875. https://doi.org/10.1039/J39710003873
dc.relation.referencesen[1] Mulwad, V.V.; Pawar, R.B. Synthesis of Biologically Active 5-Benzopyranylpyridines and Triazolopyridines. Indian J. Chem. Sect. B 2003, 42, 2901-2904. http://nopr.niscpr.res.in/handle/123456789/21765
dc.relation.referencesen[2] Abudusaimi, M.Ye.F.; Sun, J.; Miyamoto, H.; Cheng, J-F.; Oka, D. Quinolone Compound. WO 2013029548, March 7, 2013.
dc.relation.referencesen[3] Bassyouni, F.A.; Tawfik, H.A.; Hamed, A.R.; Soltan, M.M.; ElHefnawi, M.; ElRashedy, A.A.; Moharam, M.E.; Rehim, M.A. Synthesis, Antioxidant, and Antimicrobial Activities of New 2-(1,5,6-Trimethyl-1H-benzo[d]imidazole-2-carbonyl)-2,3-dihydro-1H-pyrazole-4-carbonitriles, (1,3,4-Oxadiazol-2-yl)-1H-benzo[d]-imidazol-5-yl)(phenyl)methanones, and (1,3,4-Oxadiazol-2-yl)-1,5-dihydro-[1,2,4]triazolo[1,5-a]pyridine-8-carbonitriles: QSAR and Molecular Docking Analysis. Egypt Pharm. J. 2012, 11, 80-92.
dc.relation.referencesen[4] Azzam, R.A.; Elgemeie, G.H. Synthesis and Antimicrobial Evaluation of Novel N-Substituted 4-Ethylsulfanyl-2-pyridones and Triazolopyridines. Med Chem Res. 2019, 28, 62–70. https://doi.org/10.1007/s00044-018-2264-z
dc.relation.referencesen[5] El-Adasy, A.A.; Hussein, A.M.; Ishak, E.A.; Hafiz, I.S.A.; Gawish, E.H.; Elapasery, M.A.; El-Gaby, M.S.A. Synthesis and Biological Evaluation of New 1,2,4-Triazolo[1,5-a] pyridine and 1,2,4-Triazolo[1,5-a] isoquinoline Derivatives Bearing Diphenyl Sulfide Moiety as Antimicrobial Agents. Egypt. J. Chem. 2021, 64, 913-921.
dc.relation.referencesen[6] Kuroyanagi, J-I.; Kanai, K.; Sugimoto, Y.; Fujisawa, T.; Morita, C.; Suzuki, T.; Kawakami, K.; Takemura, M. Novel Antifungal Agents: Triazolopyridines as Inhibitors of b-1,6-Glucan Synthesis. Bioorg. Med. Chem. 2010, 18, 5845-5854. https://doi.org/10.1016/j.bmc.2010.06.096
dc.relation.referencesen[7] Kawakaki, K.; Kanai, K.; Fujisawa, T.; Morita, C.; Suzuki, T. Fungicidal Heterocyclic Compounds. EP 1717238, November 2, 2006.
dc.relation.referencesen[8] Mekheimer, R.A.; Sayed, A.A.R.; Ahmed, E.A. Novel 1,2,4-Triazolo[1,5-a]pyridines and Their Fused Ring Systems Attenuate Oxidative Stress and Prolong Lifespan of Caenorhabiditis elegans. J. Med. Chem. 2012, 55, 4169-4177. https://doi.org/10.1021/jm2014315
dc.relation.referencesen[9] Mekheimer, R.A.; Sayed, A.A.R.; Ahmed, E.A.; Sadek, K.U. Synthesis and Characterization of New 1,2,4-Triazolo[1,5-a]-pyridines That Extend the Life Span of Caenorhabiditis elegans via Their Anti-Inflammatory/Antioxidant Effects. Arch. Pharm. Chem. Life Sci. 2015, 348, 650-665. https://doi.org/10.1002/ardp.201500069
dc.relation.referencesen[10] Ismail, M.M.F.; Khalifa, N.M.; Fahmy, H.H.; EL-Sahrawy, H.M.; Nossier, E.S. Anticancer Evaluation of Novel 1,3,4-Trisubstituted Pyrazole Candidates Bearing Different Nitrogenous Heterocyclic Moieties. Biomedical Research 2016, 27, 1087-1093.
dc.relation.referencesen[11] Flohr, A.; Groebke Zbinden, K.; Kuhn, B.; Lerne, C.; Rudolph, M.; Schaffhauser, H. Triazolo Compounds as PDE10 Inhibitors. WO 2013178572, December 5, 2013.
dc.relation.referencesen[12] Wu, L.; Shen, B.; Li, J.; Li, Z.; Liu, K.; Zhang, F.; Yao, W. Heterocyclic Compounds as Immunomodulators. WO 2017070089, April 27, 2017.
dc.relation.referencesen[13] Emmitte, K.A.; Lindsley, C.W.; Conn, P.J.; Felts, A.S.; Rodri-guez, A.L.; Smith, K.A.; Jones, C.K. Substituted Imidazopyridine and Triazolopyridine Compounds as Negative Allosteric Modula-tors of mGluR5. US 99844542, December 19, 2017.
dc.relation.referencesen[14] Felt, A.S.; Rodriguez, A.L.; Morrison, R.D.; Bollinger, K.A.; Venable, D.F.; Blobaum, A.L.; Byers, F.W.; Thompson Gray, A.; Daniels, J.S.; Niswender, C.M.; et al. Discovery of Imidazo[1,2-a]-, [1,2,4]Triazolo[4,3-a]-, and [1,2,4]Triazolo[1,5-a]pyridine-8-carboxamide Negative Allosteric Modulators of Metabotropic Glutamatereceptor Subtype 5. Bioorganic Med. Chem. Lett. 2017, 27, 4858-4866. https://doi.org/10.1016/j.bmcl.2017.09.042
dc.relation.referencesen[15] He, Z.; Zhang, J.; Guo, Y.; Fang, F.; Lu, J.; Cao, L.; Hu, H.; Li, X.; Xu, K. Triaryl[1,2,4]triazole[1,5-a]pyridine Derivate and Preparation Method Thereof. CN 106543175, March 29, 2017.
dc.relation.referencesen[16] Lv, J.; He, Z.; Zhang, J.; Guo. Y.; Han. Z.; Bao, X. One-pot Synthesis of [1, 2, 4] Triazolo[1,5-a]pyridines from Azines and Benzylidenemalononitriles via Copper-Catalyzed Tandem Cycliza-tion. Tetrahedron 2018, 74, 3996-4004. https://doi.org/10.1016/j.tet.2018.06.002
dc.relation.referencesen[17] Jones, G.; Sliskovic D.R. The Chemistry of the Triazolopyri-dines. Chem. Inf.-Dienst 1983, 34, 79-143. https://doi.org/10.1002/Chin.198420363
dc.relation.referencesen[18] Jones, G. The Chemistry of the Triazolopyridines: An Update. Adv. Heterocycl. Chem. 2002, 100, 1-70. https://doi.org/10.1016/S0065-2725(02)83003-3
dc.relation.referencesen[19] Vorobyov, A.Yu. Methods of Synthesis of [1,2,4]Triazolo[1,5-a]pyridines (Microreview). Chem. Heterocycl. Compd. 2019, 55, 695-697. https://doi.org/10.1007/s10593-019-02522-5
dc.relation.referencesen[20] Vercek, B.; Leban, I.; Stanovnik, B.; Tisler, M. Neighboring group Interaction in ortho-Substituted Heterocycles. 2. 1,2,4-Oxadiazolylpyridines and Pyrido[2, 3-d]pyrimidine 3-Oxides. J. Org. Chem. 1979, 44, 1695-1699. https://doi.org/10.1021/jo01324a024
dc.relation.referencesen[21] Phadke, R.C.; Rangnekar, D.W. A Novel, One-Step Synthesis of [1,2,4]Triazolo[1,5-a]pyridine Derivatives. Synthesis 1986, 10, 860-862. https://doi.org/10.1055/s-1986-31808
dc.relation.referencesen[22] Ibrahim, M.A.; El-Gohary, N.M. Heterocyclization with Some Heterocyclic Diamines: Synthetic Approaches for Nitrogen Bridge-head Heterocyclic Systems. HeteroCycles 2014, 89, 1125-1157. https://doi.org/10.3987/REV-13-790
dc.relation.referencesen[23] Khalifa, N.M.; Abdel-Rahman, A.A-H.; Abd-Elmoez, S.I.; Fathalla, O.A.; Abd El-Gwaad, A.A. A Convenient Synthesis of Some New Fused Pyridine and Pyrimidine Derivatives of Antim-icrobial Profiles. Res Chem Intermed. 2015, 41, 2295-2305. https://doi.org/10.1007/s11164-013-1347-1
dc.relation.referencesen[24] Suresh, M.; Lavanya, P.; Rao, C.V. Synthesis and Pharmacological Evaluation of Novel 2H/6H-Thiazolo-[3’,2’:2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile Derivatives. Arabian J. Chem. 2016, 9, 136-142. https://doi.org/10.1016/j.arabjc.2011.02.004
dc.relation.referencesen[25] Callejo, M.J.; Lafuente, P.; Martin-Leon, N.; Quinteiro, M.; Seoane, C.; Soto, J.L. A Convenient Preparation of [1,2,4]Triazolo[l,5-a]pyridines from Acetohydrazide Derivatives. Synthetic and Mechanistic Aspects. J. Chem. Soc., Perkin Trans. I. 1990, 1687-1690. https://doi.org/10.1039/P19900001687
dc.relation.referencesen[26] Ibrahim, H.M.; Behbehani, H.; Arafa, W.A.A. A Facile, Practical and Metal-Free Microwave Assisted Protocol for mono- and bis-[1,2,4]Triazolo[1,5-a]pyridines Synthesis Utilizing 1-Amino-2-imino-pyridine Derivatives as Versatile Precursors. RSC Adv. 2020, 10, 15554-15572. https://doi.org/10.1039/D0RA02256J
dc.relation.referencesen[27] Kockritz, P.; Riemer, B.; Michler, A.; Hassoun, A.; Liebscher, J. Synthesis of Pyrazolo[1,5-a]pyridines and Pyrazolo[1,5-c]pyrimidines by Reaction of Heterocyclic Amidrazones with 1,3-Dicarbonyl Compounds. J. Heterocycl. Chem. 1994, 31, 1157-1160. https://doi.org/10.1002/jhet.5570310510
dc.relation.referencesen[28] Patzel, M.; Liebscher, J. Synthesis of Heterocycles by Reaction of Semicyclic 2-Aza-3-methylthio-propeniminium Salts with 1,4- and 1,5-Binucleophiles. J. Prakt. Chem. 1991, 333, 149-151. https://doi.org/10.1002/prac.19913330138
dc.relation.referencesen[29] Behbehani, H.; Ibrahim, H.M. Pyrido[1,2-b]indazole Deriva-tives through AcOH and O2-Promoted Cross-dehydrogenative Coupling Reactions between 1,3-Dicarbonyl Compounds and N-Amino-2-iminopyridines. ACS Omega 2019, 4, 15289-15303. https://doi.org/10.1021/acsomega.9b02430
dc.relation.referencesen[30] Khomenko, D.M.; Shokol, T.V.; Doroshchuk, R.O.; Starova, V.S.; Raspertova, I.V.; Shova, S.; Lampeka, R.D.; Volovenko, Yu.M. An Alternative Approach to the Synthesis of [1,2,4]Triazolo[1,5-a]-pyridine-8-carbonitriles, their Crystal Struc-ture and DFT Calculations. J. Het.Chem. 2021, 58, 1278-1285. https://doi.org/10.1002/jhet.4256
dc.relation.referencesen[31] Chuiguk, V.A.; Fedotov, K.V. Formation of Condensed Pyridinium Cycles in the Reaction of Protonized Cyano- and Nitromethylazoles with 1,3-Diketones. Ukr. Khim. Zh. 1980, 46, 1306-1310.
dc.relation.referencesen[32] Volovenko, Y.M.; Shokol, T.V. Convenient Method for the Annelation of a Pyridine Ring to Azaheterocyclic Systems. Chem. Heterocycl. Compd. 2003, 39, 545-546. https://doi.org/10.1023/A:1024738018872
dc.relation.referencesen[33] Trottmann, G.H.; Hunkeler, W.; Jakob-Roetne, R.; Kilpatrick, G.J.; Nettekoven, M.H.; Riemer, C., inventor; Hoffmann-La Roche Inc., assignee. Amino-triazolopyridine Derivatives. US 6355653, March 12, 2002.
dc.relation.referencesen[34] Milokhov, D.S.; Khilya, O.V.; Turov, A.V.; Medviediev, V.V.; Shishkin, O.V.; Volovenko, Yu.M. Hydroxypropyl Substituted Nitrogen Bridgehead Fused Cyanopyridines. Tetrahedron 2014, 70, 1214-1222. https://doi.org/10.1016/j.tet.2013.12.074
dc.relation.referencesen[35] Zribi, L.; Zribi, F.; Marco-Contelles, J.; Chabchoub, F.; Ismaili, L. Facile One-Pot Synthesis of New [1,2,4]Triazolo[1,5-a]pyridine Derivatives by Ultrasonic Irradiation. Synth. Commun. 2017, 47, 1934-1939. https://doi.org/10.1080/00397911.2017.1357078
dc.relation.referencesen[36] Martin, N.; Quinteiro, M.; Seoane, C.; Soto, J.L.; Fonseca, I.; Florencio, F.; Sanz, J. Two Rings in One Step: A Novel 1,2,4-Triazolo[1,5-a]pyridone with an Unusual Crystal Structure. J. Org. Chem. 1990, 55, 2259-2262. https://doi.org/10.1021/jo00294a058
dc.relation.referencesen[37] Hadi, A.; Martin, N.; Seoane, C.; Soto, J.L.; Albert, A.; Cano, F. Synthesis and Crystal Structure of Piperidinium 2-Aryl[1,2,4]triazolo[1,5-a]pyridinides and their Neutralization to 2-Aryl[1,2,4]triazolo[1,5-a]-pyridines. J. Heterocycl. Chem. 1992, 29, 1229-1235. https://doi.org/10.1002/jhet.5570290531
dc.relation.referencesen[38] Hadi, A. Synthesis of Novel [1,2,4]Triazolo[1,5-a]pyridines via Concerted Reactions Between 2-Cinnamoyl-2-cyanoacetohydrazide and α-Cyanocinamonitriles. J. Kerbala Univ. 2011, 9, 55-75.
dc.relation.referencesen[39] Yamazaki, C.; Miyamoto, Y.; Sakima, H. Cyclization of Isothiosemicarbazones. Part 10. A Novel Route to 2-Amino[1,2,4]triazolo[1,5-a]pyridine Derivatives. J. Chem. Soc., Perkin Trans. 1 1994, 825-828. https://doi.org/10.1039/P19940000825
dc.relation.referencesen[40] Alizadeh, A.; Saberi, V.; Mokhtari, J. A Simple One-Pot Procedure for the Synthesis of 1,2,4-Triazolo[1,5-a]pyridines via Pseudo Five-Component Reactions Catalyzed by Molecular Iodine. Synlett 2013, 24, 1825-1829. https://doi.org/10.1055/s-0033-1339333
dc.relation.referencesen[41] Boyd, G.V.; Summers, A.J.H. The Action of Amines on I ,3,4-Oxadiazolium Salts. J. Chem. Soc. P. 1971, 409-414. https://doi.org/10.1039/J39710000409
dc.relation.referencesen[42] Boyd, G.V.; Dando, S.R. The Action of Cyanamide on 1,3,4-Oxadiazolium and Pyrylium Salts. J. Chem. Soc. P. 1971, 3873-3875. https://doi.org/10.1039/J39710003873
dc.relation.urihttp://nopr.niscpr.res.in/handle/123456789/21765
dc.relation.urihttps://doi.org/10.1007/s00044-018-2264-z
dc.relation.urihttps://doi.org/10.1016/j.bmc.2010.06.096
dc.relation.urihttps://doi.org/10.1021/jm2014315
dc.relation.urihttps://doi.org/10.1002/ardp.201500069
dc.relation.urihttps://doi.org/10.1016/j.bmcl.2017.09.042
dc.relation.urihttps://doi.org/10.1016/j.tet.2018.06.002
dc.relation.urihttps://doi.org/10.1002/Chin.198420363
dc.relation.urihttps://doi.org/10.1016/S0065-2725(02)83003-3
dc.relation.urihttps://doi.org/10.1007/s10593-019-02522-5
dc.relation.urihttps://doi.org/10.1021/jo01324a024
dc.relation.urihttps://doi.org/10.1055/s-1986-31808
dc.relation.urihttps://doi.org/10.3987/REV-13-790
dc.relation.urihttps://doi.org/10.1007/s11164-013-1347-1
dc.relation.urihttps://doi.org/10.1016/j.arabjc.2011.02.004
dc.relation.urihttps://doi.org/10.1039/P19900001687
dc.relation.urihttps://doi.org/10.1039/D0RA02256J
dc.relation.urihttps://doi.org/10.1002/jhet.5570310510
dc.relation.urihttps://doi.org/10.1002/prac.19913330138
dc.relation.urihttps://doi.org/10.1021/acsomega.9b02430
dc.relation.urihttps://doi.org/10.1002/jhet.4256
dc.relation.urihttps://doi.org/10.1023/A:1024738018872
dc.relation.urihttps://doi.org/10.1016/j.tet.2013.12.074
dc.relation.urihttps://doi.org/10.1080/00397911.2017.1357078
dc.relation.urihttps://doi.org/10.1021/jo00294a058
dc.relation.urihttps://doi.org/10.1002/jhet.5570290531
dc.relation.urihttps://doi.org/10.1039/P19940000825
dc.relation.urihttps://doi.org/10.1055/s-0033-1339333
dc.relation.urihttps://doi.org/10.1039/J39710000409
dc.relation.urihttps://doi.org/10.1039/J39710003873
dc.rights.holder© Національний університет “Львівська політехніка”, 2023
dc.rights.holder© Khomenko D., Shokol T., Doroshchuk R., Raspertova I., Lampeka R., Volovenko Yu., 2023
dc.subjectамінопіридини
dc.subjectконденсація
dc.subjectпохідні гідразину
dc.subject[1
dc.subject2
dc.subject4]триазоло[1
dc.subject5-a]піридин-8-карбонітрили
dc.subject2-(1H-1
dc.subject2
dc.subject4-триазол-5-іл)ацетонітрил
dc.subjectaminopyridines
dc.subjectcondensation
dc.subjecthydrazine derivatives
dc.subject[1
dc.subject2
dc.subject4]triazolo[1
dc.subject5-a]pyridine-8-carbonitriles
dc.subject2-(1H-1
dc.subject2
dc.subject4-triazol-5-yl)acetonitrile
dc.titleStrategies for the Synthesis of [1,2,4]Triazolo[1,5-a]pyridine-8-carbonitriles
dc.title.alternativeСтратегії синтезу [1,2,4]триазоло [1,5-a]піридин-8-карбонітрилів
dc.typeArticle

Files

Original bundle

Now showing 1 - 2 of 2
Thumbnail Image
Name:
2023v17n2_Khomenko_D-Strategies_for_the_Synthesis_294-303.pdf
Size:
873.15 KB
Format:
Adobe Portable Document Format
Thumbnail Image
Name:
2023v17n2_Khomenko_D-Strategies_for_the_Synthesis_294-303__COVER.png
Size:
543.98 KB
Format:
Portable Network Graphics

License bundle

Now showing 1 - 1 of 1
No Thumbnail Available
Name:
license.txt
Size:
1.83 KB
Format:
Plain Text
Description: