Annelation reactions of pentafluorobenzonitrile

Annelation reactions between pentafluorobenzonitrile and N,N-dimethylethylene diamine and 3-methyl picoline gave [6,6]-bicyclic and [6,5,6]-tricyclic ring-fused systems, respectively. Reaction of 4-morpholino tetrafluorobenzonitrile with hydrazine and phenyl hydrazine gave [5,6] ring-fused systems arising from a tandem S_NAr and cyclisation process involving annelation onto the pendant cyano group providing an indication of the synthetic possibilities for heterocycle formation using the pentafluorobenzonitrile scaffold.