Friedlander substrate

The Friedlander reaction makes available a wide variety of 1,10-phenanthrolines and other macrocyclic chelators (e.g. 33, 34 and 35). These polyaza-aromatic rings can bind a variety of metals or organic substrates. 

In the simplest of these, jS-enaminones are synthesized (equation 129) by the addition of amines to 1,3-diketones or /3-ketoesters. The reaction has been apphed to the Friedlander synthesis of quinolines by condensation of the enaminone and other carbonyl present in the substrate. Substituted pyrroles in equation (130) can be obtained as well when a propargyl group is present, by addition of the enaminone to the triple bond. Alcohols, thiols, and secondary phosphines have been also tested as nucleophiles with good results. A particularly interesting case is found in the condensation of indoles with 1,3-diketones to give substituted indol derivatives in equation (131). ... 

Suh Y J, Ullinann M, Friedlander S K and Park K Y (2001) Elastic Behavior of Nano-particle Chain Aggregates (NCA) Effects of Substrate on NCA Stretching and First Observations by a High-Speed Camera, J Phys Chem B 105 11796-11799. 

---