Cyclocondensation Reactions of a Bifunctional Monomer Bearing a Nucleophilic Hydrazine and Electrophilic Ketoester Pair

Abstract

An approach to combine monomer units forming heterocyclic linkages is described. A bifunctional monomer bearing a nucleophilic hydrazine and electrophilic ketoester pair was designed and synthesized. The monomer was employed to construct oligomeric products containing pyridazinone linkages via cyclocondensation reactions. The cyclocondensation oligomerization yielded up to pentamers including macrocycles. Regiochemical studies with model compounds revealed that the cyclocondensation occurred via a hydrazone intermediate when conducted under acidic conditions.

Keywords: cyclocondensation, Bifunctional, Heterocycles, Pyridazinone, Oligomerization