Water – the best solvent for DMAP-mediated dual cyclization towards metal-free first synthesis of fully substituted phthalimides

Abstract

4-Dimethylaminopyridine (DMAP) in water medium is exploited for construction of an intermolecular assembly of acetyl/benzoyl acetanilides and alkynes for a new [2 + 2 + 2] and [3 + 2] cascade dual annulation. DMAP is expected to act as a promoter for dual annulation and carrier to transport in situ generated water and alcohol from the lipophilic nanoreactors to the water surroundings leading to the first rapid synthesis of fully substituted phthalimide analogues. Insights into the rapid reaction are illustrated in our controlled experiments, dynamic light scattering (DLS) and UV–vis study.