Efficient Synthesis Of 5-Substituted Ethyl 1,2,4-Triazole-3-Carboxylates

Dmytro M. Khomenko, Roman O. Doroschuk, Rostyslav D. Lampeka

Abstract


Easily accessible carboxylic acid hydrazides undergo cyclocondensation with ethyl carbethoxyformimidate, giving 5-substituted ethyl 1,2,4-triazole-3-carboxylates. These are important building blocks in organic synthesis. The approach we used to obtain title compounds made possible synthesis of 3-(2-aminophenyl)-1,2,4-triazole


Keywords


1,2,4-triazole; carbethoxyformimidate; acylamidrazone; cyclocondensation; acylhydrazide

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References


Kharb R, Sharma P, Yar M. Pharmacological significance of triazole scaffold. Journal of Enzyme Inhibition and Medicinal Chemistry 2010;26(1):1-21. https://doi.org/10.3109/14756360903524304

Kini G, Robins R, Avery T. Synthesis and antitumor activity of ribavirin imidates. New facile synthesis of ribavirin amidine (1-.beta.-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine hydrochloride). J. Med. Chem. 1989;32(7):1447-1449. https://doi.org/10.1021/jm00127a008

Witkowski J, Robins R, Sidwell R, Simon L. Design, synthesis, and broad spectrum antiviral activity of 1-.beta.-D-ribofuranosyl-1,2,4-triazole-3-carboxamide and related nucleosides. J. Med. Chem. 1972;15(11):1150-1154. https://doi.org/10.1021/jm00281a014

Huynh-Dinh T, Igolen J, Bisagni E, Marquet J, Civier A. Synthesis of C-nucleosides. Part 14. 5(3)-Glycosyl-1,2,4-triazole-3(5) carboxamides as analogues of ribavirin. Journal of the Chemical Society, Perkin Transactions 1 1977;(7):761. https://doi.org/10.1039/p19770000761

Cesar J, Sollner M. Use of 3,5-Disubstituted 1,2,4-Triazoles for the Synthesis of Peptidomimetics. Synthetic Communications 2000;30(22):4147-4158. https://doi.org/10.1080/00397910008087031

Bacchi A, Carcelli M, Compari C, Fisicaro E, Pala N, Rispoli G, Rogolino D, Sanchez T, Sechi M, Neamati N. HIV-1 IN Strand Transfer Chelating Inhibitors: A Focus on Metal Binding. Mol. Pharmaceutics 2011;8(2):507-519. https://doi.org/10.1021/mp100343x

Oliver J, Sonnet P. Improved routes to methyl 4-methylimidazole-2-carboxylate and methyl 5-methyl-1,2,4-triazole-3-carboxylate. The Journal of Organic Chemistry 1973;38(7):1437-1438. https://doi.org/10.1021/jo00947a052

Vaněk T, Velková V, Gut J. Preparation of 3- and 3,5-substituted 1,2,4-triazoles. Collect. Czech. Chem. Commun. 1984;49(11):2492-2495. https://doi.org/10.1135/cccc19842492

McKillop A, Henderson A, S. Ray P, Avendano C, Molinero E. Heterocyclic synthesis using ethyl carboethoxyformimidate. Tetrahedron Letters 1982;23(33):3357-3360. https://doi.org/10.1016/s0040-4039(00)87614-5

Dost J, Stein J, Heschel M. Zur Herstellung von 5-substituierten 1,2,4-Triazol-3-carbonsäurederivaten aus Oxalsäureethylester-N1-acylamidrazonen. Z. Chem. 2010;26(6):203-204. https://doi.org/10.1002/zfch.19860260603

Vemishetti P, Leiby R, Abushanab E, Panzica R. A practical synthesis of ethyl 1,2,4-triazole-3-carboxylate and its use in the formation of chiral 1′,2′- seco -nucleosides of ribavirin . Journal of Heterocyclic Chemistry 1988;25(2):651-654. https://doi.org/10.1002/jhet.5570250253

Lippa B, Pan G, Corbett M, Li C, Kauffman G, Pandit J, Robinson S, Wei L, Kozina E, Marr E, Borzillo G, Knauth E, Barbacci-Tobin E, Vincent P, Troutman M, Baker D, Rajamohan F, Kakar S, Clark T, Morris J. Synthesis and structure based optimization of novel Akt inhibitors. Bioorganic & Medicinal Chemistry Letters 2008;18(11):3359-3363. https://doi.org/10.1016/j.bmcl.2008.04.034

Speake J, Navas F, Bishop M, Garrison D, Bigham E, Hodson S, Saussy D, Liacos J, Irving P, Sherman B. 2-(Anilinomethyl)imidazolines as α1 adrenergic receptor agonists: α1a subtype selective 2′-heteroaryl compounds. Bioorganic & Medicinal Chemistry Letters 2003;13(6):1183-1186. https://doi.org/10.1016/s0960-894x(03)00050-7

Volovel`ski LN, Knorozova GV. J Gen Chem USSR (Engl Trans.). 1964;34(1):343–347.




DOI: https://doi.org/10.17721/fujcV4I2P28-32

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