Aryl amines reacted with enaminones like (2-chloro-3-pyridinyl)[2-(1-pyrrolidinyl)-1- cyclopenten-1-yl] methanone, and the transaminated products cyclized to aryl-substituted pyridones like 6, 7, 8, 9-tetrahydro-9-phenyl-5H-cyclopenta [b][1, 8] naphthyridin-5-one. The starting enaminones rearranged thermally, also forming pyridones, for example 9-(4- chlorobutyl)-6, 7, 8, 9-tetrahydro-5H-cyclopenta [b][1, 8] naphthyridin-5-one.
[Jones, Alan M.; Lorion, Magali M.; Lebl, Tomas; Slawin, Alexandra M.Z.; Philp, Douglas; Westwood, Nicholas J. Tetrahedron, 2010 , vol. 66, # 51 p. 9667 - 9674]