Abstract
The title compound, C13H14N4O, was developed using the reaction of salicyl-aldehyde and 3-amino-5-cyclo-butyl-1,2,4-triazole in ethanol under microwave irradiation. This eco-friendly microwave-promoted method proved to be efficient in the synthesis of 2-{[(E)-(3-cyclo-butyl-1H-1,2,4-triazol-5-yl)imino]-meth-yl}phenol in good yields and purity. The title compound is a Schiff base that exists in the phenol-imine tautomeric form and adopts an E configuration. The three independent mol-ecules in the asymmetric unit (A, B and C) are not planar, the cyclo-butyl and the phenol-imine rings are twisted to each other making a dihedral angle of 67.8 (4)° in mol-ecule A, 69.1 (2)° in mol-ecule B and 89.1 (2)° in mol-ecule C. In each mol-ecule an intra-molecular O-H⋯N hydrogen bond is present, forming an S(6) ring motif. A Hirshfeld surface analysis was performed to investigate the contributions of the different inter-molecular contacts within the supra-molecular structure. The major inter-actions are H⋯H (53%), C⋯H (19%) and N⋯H (17%) for mol-ecule A, H⋯H (50%), N⋯H (20%) and C⋯H (20%) for mol-ecule B and H⋯H (57%), C⋯H (14%) and N⋯H (13%) for mol-ecule C.
Highlights
The title compound, C13H14N4O, was developed using the reaction of salicylaldehyde and 3-amino-5-cyclobutyl-1,2,4-triazole in ethanol under microwave irradiation. This eco-friendly microwave-promoted method proved to be efficient in the synthesis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol in good yields and purity
The title compound is a Schiff base that exists in the phenol–imine tautomeric form and adopts an E configuration
Taking into account the above considerations, it was decided to merge the chemistry of both parts by reacting 3-amino-5-cyclobutyl-1,2,4-triazole with salicylaldehyde to develop an efficient green protocol for the synthesis of 2-[(E)-(5-cyclobutyl-2H-1,2,4-triazol-3-ylimino)methyl]phenol
Summary
Imines (Schiff bases) have been extensively used as analytical and medicinal materials (Bulbul et al, 2017; Singh, 2021). 1,2,4-Triazoles possess a number of medicinal attributes (Aggarwal & Sumran, 2020). Imines (Schiff bases) have been extensively used as analytical and medicinal materials (Bulbul et al, 2017; Singh, 2021). 1,2,4-Triazoles possess a number of medicinal attributes (Aggarwal & Sumran, 2020). Taking into account the above considerations, it was decided to merge the chemistry of both parts by reacting 3-amino-5-cyclobutyl-1,2,4-triazole with salicylaldehyde to develop an efficient green protocol for the synthesis of 2-[(E)-(5-cyclobutyl-2H-1,2,4-triazol-3-ylimino)methyl]phenol. An eco-friendly protocol for the synthesis of Schiff bases from 3-amino-5-cyclobutyl-1,2,4triazole and salicylaldehyde in ethanol under microwave irradiation was developed. 2-[(E)-(5-cyclobutyl2H-1,2,4-triazol-3-ylimino)methyl]phenol was characterized by single crystal X-ray diffraction and investigated using Hirshfeld surface analysis.
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