Functionalization of the 1,8-Naphthalimide Core with Weak Nucleophiles

A new synthetic strategy for the functionalization of the 1,8-naphthalimide core with weak nucleophiles was developed and is presented herein. By selection of the appropriate base and reaction temperature, access to difluoro, dialkoxy (including with a fused dioxa ring), and mixed fluoro-alkoky and alkoxy-hydroxy derivatives was achieved. All of the reactions proceed rapidly on a gram scale, affording the target products in a high yield (80-97%) and purity from inexpensive, commercially available starting compounds and reagents.