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

Authors

  • Dmytro M. Khomenko Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Str. 64, Kyiv, Ukraine
  • Roman O. Doroschuk Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Str. 64, Kyiv, Ukraine
  • Rostyslav D. Lampeka Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Str. 64, Kyiv, 01033, Ukraine

DOI:

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

Keywords:

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

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

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.

Downloads

Published

2016-12-27

Issue

Vol. 4 No. 2 (2016)

Section

Short Communication

License

Authors who publish with this journal agree to the following terms:

  • Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

  • Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.

  • Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).