Research Article

Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles

Volume: 41 Number: 3 September 1, 2021
TR EN

Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles

Abstract

The aim of the work was to describe the method of combining two 1,2,4-triazole systems in a molecule, the alkylation reaction of the thiol group to obtain the previ- ously undiscovered S-derivatives of 1,2,4-triazole and the fragmentation pathway of the substances under hard ionization using gas chromatography-mass spectrom- etry. The structures of the synthesized compounds were confirmed by elemental analysis, 1H and 13C NMR spectroscopy and GC-MS analysis. The characteristic signals for S-alkyl residues were observed in the region typical for aliphatic com- pounds. The fragmentation of molecules was represented by the gradual cleavage of radicals and the opening of the second 1,2,4-triazole heterocycle.

Keywords

References

  1. 1. 1. Orlewska, C.; Pancechowska-Ksepko, D.; Foks, H.; Zwolska, Z.; Augustynowicz-Kopec, E. Reactivity of N 1-Dithioester Substituted Pyridinand Pyrazincarboxamidrazones. Phosphorus, Sulfur, and Silicon and the Related Elements, 2006, 181(4), pp. 737–744. https://doi.org/10.1080/10426500500270065
  2. 2. Pellizzari, G.; Gazz Chim Ital, 1911, no. 41, pp. 93.
  3. 3. Ji Ram, V.; Sethi, A.; Nath, M.; Pratap, R. Five-Membered Heterocycles. The Chemistry of Heterocycles, 2019, pp. 365. https://doi.org/10.1016/b978-0-08-101033-4.00005-x
  4. 4. Ueda, S.; Nagasawa, H. Facile synthesis of 1,2,4-triazoles via a copper-catalyzed tandem addition−oxidative cyclization. Journal of the American Chemical Society, 2009, 131(42), pp. 15080-15081. DOI: https://doi.org/10.1021/ja905056z
  5. 5. Huang, H.; Guo, W.; Wu, W.; Li, C.-J.; Jiang, H. Copper-catalyzed oxidative C(sp3)–H functionalization for facile synthesis of 1,2,4-triazoles and 1,3,5-triazines from amidines. Organic Letters, 2015, 17(12), pp. 2894-2897. DOI: https://doi.org/10.1021/acs.orglett.5b00995
  6. 6. Castanedo, G. M.; Seng, P. S.; Blaquiere, N.; Trapp, S.; Staben, S. T. Rapid synthesis of 1,3,5-substituted 1,2,4-triazoles from carboxylic acids, amidines, and hydrazines. The Journal of Organic Chemistry, 2011, 76(4), pp. 1177-1179. DOI: https://doi.org/10.1021/jo1023393
  7. 7. Vidavalur, S.; Nakka, M.; Tadikonda, R.; Rayavarapu, S.; Sarakula, P. A Simple and efficient synthesis of 3,4,5-trisubstituted/n-fused 1,2,4-triazoles via ceric ammonium nitrate catalyzed oxidative cyclization of amidrazones with aldehydes using polyethylene glycol as a recyclable reaction medium. Synthesis, 2014, 47(04), pp. 517-525. DOI: https://doi.org/10.1055/s-0034-1378909
  8. 8. Minozzi, C.; Caron, A.; Grenier-Petel, J.; Santandrea, J.; Collins, S. Heteroleptic copper(I)-based complexes for photocatalysis: combinatorial assembly, discovery, and optimization. Angewandte Chemie International Edition, 2018, 57(19), pp. 5477-5481. DOI: 10.1002/anie.201800144

Details

Primary Language

English

Subjects

Pharmacology and Pharmaceutical Sciences

Journal Section

Research Article

Authors

Publication Date

September 1, 2021

Submission Date

July 20, 2021

Acceptance Date

October 4, 2021

Published in Issue

Year 2021 Volume: 41 Number: 3

APA
Karpun, Y. (2021). Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles. Hacettepe University Journal of the Faculty of Pharmacy, 41(3), 150-161. https://doi.org/10.52794/hujpharm.973420
AMA
1.Karpun Y. Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles. HUJPHARM. 2021;41(3):150-161. doi:10.52794/hujpharm.973420
Chicago
Karpun, Yevhen. 2021. “Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles”. Hacettepe University Journal of the Faculty of Pharmacy 41 (3): 150-61. https://doi.org/10.52794/hujpharm.973420.
EndNote
Karpun Y (September 1, 2021) Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles. Hacettepe University Journal of the Faculty of Pharmacy 41 3 150–161.
IEEE
[1]Y. Karpun, “Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles”, HUJPHARM, vol. 41, no. 3, pp. 150–161, Sept. 2021, doi: 10.52794/hujpharm.973420.
ISNAD
Karpun, Yevhen. “Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles”. Hacettepe University Journal of the Faculty of Pharmacy 41/3 (September 1, 2021): 150-161. https://doi.org/10.52794/hujpharm.973420.
JAMA
1.Karpun Y. Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles. HUJPHARM. 2021;41:150–161.
MLA
Karpun, Yevhen. “Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles”. Hacettepe University Journal of the Faculty of Pharmacy, vol. 41, no. 3, Sept. 2021, pp. 150-61, doi:10.52794/hujpharm.973420.
Vancouver
1.Yevhen Karpun. Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles. HUJPHARM. 2021 Sep. 1;41(3):150-61. doi:10.52794/hujpharm.973420

Cited By