4-Trichloroacetyl-1,2,3-triazoles: A versatile building block for rapid assessment of carbohydrazides and rufinamide derivatives |
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Authors: | Helio G Bonacorso Francieli M Libero Fábio M Luz Maiara C Moraes Susiane Cavinatto Felipe S Stefanello Melissa B Rodrigues Nilo Zanatta Marcos AP Martins |
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Institution: | Núcleo de Química de Heterociclos – NUQUIMHE, Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil |
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Abstract: | This work reports the synthesis of a series of (1H-1,2,3-triazol-4-yl)carbohydrazides (2), which were obtained from 4-trichloroacetyl-1H-1,2,3-triazoles (1). Triazoles 1 were synthesized by 1,3-dipolar cycloaddition reaction, starting from 4-alkoxy-1,1,1-trichloroalk-3-en-2-ones and benzyl azides and easily (15 min) converted to 2 by reaction with hydrazine hydrate (73–82% yield). Carbohydrazides 2 proved to be a versatile building block for constructing a series of fluorinated heterocycles analogous to rufinamide, i.e., 1H-1,2,3-triazol-4-yl-1,3,4-oxadiazoles, a pyrrole derivative, and a 2-pyrazoline, through 4+1]–, 1+4]–, and 3+2]–cyclocondensation reactions, respectively. Finally, and according to the Lipinski’s rule of five, 2,6-difluorobenzylated 1,2,3-triazoles can be considered as potential candidates for further biological activity assays. |
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Keywords: | Triazoles Carbohydrazides Rufinamide Haloformic reactions Cyclocondensation reactions |
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