Polyaza heterocycles. Part 2. Nucleophilic substitution of halogens in halogenoquinoxalino[2,3-c]cinnolines

Abstract

10-Chloroquinoxalino[2,3-c]cinnoline readily undergoes methoxydechlorination when treated with sodium methoxide. The 1-, 2-, 3-, 4- and 9-chloro isomers are unreactive towards this reagent, but the 9,10-dichloro derivative undergoes substitution of both chlorines (the 10-position being much the more reactive). The 9- and 10-bromo analogues are both unreactive towards sodium methoxide, but the 9- and 10-fluoro analogues are both highly reactive, to the extent that it has not been possible even to isolate the 10-fluoro compound. Routes to 9- and 10-piperidinoquinoxalino[2,3-c]cinnolines are described.