Benzo[c]cinnoline derivatives. VI. Reactions of halogenobenzo[c]cinnolines with potassium amide

Abstract

The individual reactions of chloro- and iodo-benzo[cJcinnolines with potassium amide in ammonia have been shown to yield mixtures of aminobenzo[c]cinnolines. The observed courses of reaction are discussed in terms of mixed addition-elimination and elimination-addition mechanisms. A small amount of tele-substitution (1,3-substitution) has been found to occur when 4-chlorobenzo[c]- cinnoline reacts with potassium amide. Two possible mechanisms for this reaction are considered.