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

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 FTIR, 1H NMR spectroscopy and elemental analysis. Moreover, the molecular structure of 2a was determined by single-crystal X-ray diffraction.