This laboratory session introduces undergraduate students to the principles of multicomponent reactions (MCRs) and fluorescence through the one-pot four-component synthesis of a boronic acid-derived salicylidenehydrazone (BASHY) dye from nonfluorescent precursors. The proposed experiment exemplifies the atom economy, efficiency, and structural complexity of MCRs while showcasing its potential in the development of novel fluorescent architectures with applications in bioimaging and therapeutics. By combining synthetic design, mechanistic reasoning, and spectroscopic interpretation, this activity fosters active learning and strengthens students’ knowledge of fundamental chemical concepts, including the reactivity of carbonyl and amine functional groups, and structural characterization. Overall, the BASHY synthesis provides a versatile, engaging, and conceptually rich platform for teaching modern synthetic methodologies and the molecular principles of fluorescence.
Reis et al. (Tue,) studied this question.