One-Pot Synthesis of 4-Carboalkoxy-Substituted Benzo[ h]coumarins from α- A nd β-Naphthols and Their Excited-State Properties

Abstract

One-pot synthesis has been developed for 4-carboethoxybenzo[h]coumarins starting from α-/β-naphthols. Accordingly, diverse 4-carboethoxybenzocoumarins can be synthesized in moderate-to-excellent (31-75%) isolated yields. The synthesis involves initial oxidation of naphthols to the intermediary 1,2-naphthoquinones with 2-iodoxybenzoic acid followed by a cascade of reactions, namely, Wittig olefination, Michael addition, β-elimination, and cyclization. Furthermore, we have comprehensively investigated the excited-state properties of differently substituted 4-carboalkoxybenzo[h]coumarins. It is shown that they exhibit low to high fluorescence quantum yields (1-36%) and excited-state lifetimes (ca. 1-7 ns) depending on the substitution pattern and solvent employed.