One-pot synthesis of diethyl 4,4'-(1,4-phenylene)bis-(6-(halomethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates) and their bispyrrolocyclization

摘要

A one-pot synthesis of diethyl 4,4'-(1,4-phe-nylene)bis[6-(chloromethyl)-2-oxo-1,2,3,4-tetrahydropyri-midine-5-carboxylates] is proposed via three-component condensation of terephthalic aldehyde, 4-chloroacetoacetic ester, and ureas under Biginelli reaction conditions. Interaction of the obtained precursors that contain two highly reactive binucleophilic groups with primary amines leads to bis-heterocyclization with formation of (1,4-phenylene)-bis(pyrrolo[3,4-d]pyrimidine-2,5-diones).