Revisiting ring-degenerate rearrangements of 1-substituted-4-imino-1,2,3-triazoles.

摘要: The 1-substituted-4-imino-1,2,3-triazole motif is an established component of coordination compounds and bioactive molecules, but depending on the substituent identity, it can be inherently unstable due to Dimroth rearrangements. This study examined parameters governing ring-degenerate rearrangement reactions 1-substituted-4-imino-1,2,3-triazoles, expanding trends first observed by L'abbe et al. efficiency condensation between 4-formyltriazole amine reactants as well propensity imine products towards was each strongly influenced identity. It that unsymmetrical conducted at 70 °C produced up four via a dynamic equilibrium condensation, hydrolysis steps. Kinetic studies utilizing 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbaldehyde with varying amines showed rates sensitive both steric electronic factors. Such measurements were facilitated high throughput colorimetric assay directly monitor generation 4-nitroaniline byproduct.