Reactions of the dianion obtained by reductive metallation of 3,4-diphenylcinnoline

Abstract

The reductive metallation of 3,4-diphenylcinnoline (1) by sodium metal in tetrahydrofuran under an inert atmosphere to the monomeric dianion 2 has been explored, and the nucleophilicity of the disodium adduct towards various protonation, alkylation, and acylation reagents has been investigated. Generally, 2 reacts via its 1,4-positions forming 1,4-dihydro derivatives of 1.