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