JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 70 No 4 (2025): Journal of The Chilean Chemical Society
Original Research Papers

Organometallic Aminomethyl 1,2,3-Triazoles: Synthesis, Characterization and Reactivity

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  • Luis Peña,
  • David Villaman ,
  • Rodrigo Arancibia
Luis Peña
Facultad de Ciencias Químicas, Universidad de Concepción, Concepción, Chile.
David Villaman
Facultad de Ciencias Químicas, Universidad de Concepción, Concepción, Chile.
Rodrigo Arancibia
Departamento de Química Analítica e InorgánicaFacultad de Ciencias QuímicasUniversidad de Concepcion
Published April 13, 2026
Keywords
  • Organometallic-1,2,3-triazole,
  • Cyrhetrene,
  • Ferrocene,
  • Aminomethyl,
  • Reactivity
How to Cite
Peña, L., Villaman , D., & Arancibia, R. (2026). Organometallic Aminomethyl 1,2,3-Triazoles: Synthesis, Characterization and Reactivity. Journal of the Chilean Chemical Society, 70(4), 6450-6461. Retrieved from https://www.jcchems.com/index.php/JCCHEMS/article/view/2965

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Abstract

In search of new organometallic-1,2,3-triazoles, this work describes a convenient synthesis to obtain ferrocenyl and cyrhetrenyl 1,2,3-triazole derivatives containing aminomethyl fragment. On this regard, the compounds of general formulae [(η⁵-C₅H₄-(1)-1,2,3-triazole-(4)-CH₂NH₂)MLn] [where MLn =Fe(η⁵-C₅H₅) (1a), Re(CO)₃ (1b)] were obtained via tert-butoxycarbonyl (BOC) deprotection under acid conditions of the corresponding protected triazoles [(η⁵-C₅H₄-(1)-1,2,3-triazole-(4)-CH₂NH(C=O)OC(CH3)3)MLn] with MLn = Fe(η⁵-C₅H₅) (P1), Re(CO)₃ (P2)], with good yields (89–95%). In addition, the reactivity of aminomethyl compounds (1a–b) was evaluated in condensation reactions with 4-(1H-1,2,4-triazol-1-yl)benzaldehyde, isolated the Schiff bases [(η⁵-C₅H₄-(1)-1,2,3-triazole-(4)-CH₂N=CH-(1)-C₆H₄-(4)-1H-1,2,4-triazole)MLn] (2a–b) [where MLn =Fe(η⁵-C₅H₅) (2a), Re(CO)₃ (2b)] under mild reactions conditions. All compounds were characterized by FT-IR, ¹H NMR spectroscopy and elemental analysis. Moreover, the molecular structure of 2a was determined by single-crystal X-ray diffraction.

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