Abstract
Triazoles are heterocyclic, aromatic compounds used as intermediates for the synthesis of dyes, lubricants, and anticorrosion products. They are found in all aspects of drug discovery, ranging from pharmaceutical and agriculture industries to proteomic and DNA studies. Derivatives of triazole have been found to have biological activities such as anti-HIV, anti-allergenic, anti-microbial, anti-inflammatory, anti-bacterial, and anti-fungal applications. Triazoles are unique in that the molecule is an aromatic, five-membered ring containing three nitrogens. The reactivity of each nitrogen in the ring appears to be dependent upon different reaction conditions; however, the mechanism leading to the reactivity is unclear. In the literature, regioisomers result from the reaction of 3-amino-1,2,4-triazole and bi-functional electrophiles such as the conjugated acid halides. However, the products reported in the literature were not well characterized and often the issue of alternate isomers was not even investigated. This study focuses on reactions to understand both the reactivity of this interesting nucleophile and the mechanism by which products are formed (and possibly thereby leading to some level of control over reaction orientation). Reactions of 3-amino-1,2,4-triazole with two different conjugated acid halides (trans-cinnamoyl chloride and trans-crotonyl chloride) are investigated in this study under different synthetic conditions, varying solvent, reaction time, and temperature to provide a better understanding of the reactivity of this system. Isolated products were purified using flash column chromatography and fully analyzed by GC-MS, 1H NMR, 13C NMR, 1H-13C HSQC, 15N NMR, and 1H-15N HMBC analysis. The full characterization of the products will allow for a better understanding of the reactivity of the 3-amino-1,2,4-triazole nucleophile.