Facile one-pot synthesis of novel imidates as multifunctional organic fluorescent materials

Abstract

Imidates have enormous applications in the synthesis of natural products and nitrogen-containing heterocyclic compounds, as well as in drug development. However, there is currently a lack of green and efficient synthesis methods for imidate compounds. We present a novel one-pot synthesis of multifunctional organic fluorescent imidates from quinolinium salt derivatives, nitrosoarenes and alcohols. This method has the advantages of operational simplicity, mild reaction conditions, metal-free catalysis, a wide substrate scope (43 examples) and excellent isolated yields (up to 93%). Meanwhile, quinolinium-imidates exhibit good fluorescence intensity and excellent chemical stability, which makes them suitable for application in living cells, and in particular, imidate 4v can target the endoplasmic reticulum with high selectivity.