Application of the Pictet-Spengler reaction to aryl amine substrates linked to deactivated aromatic heterosystems

Three new substrates with an aryl amine moiety attached to quinoxalines. triazoles and tetrazoles either via C or N have been used for the Pictet-Spengler reaction. The substrates have been designed by applying the concept of aryl amine attached to a deactivated heteroaromatic ring' in a manner to facilitate endo cyclization. This is in contrast to the substrates used traditionally and reported earlier by us that are based on either aliphatic or aryl amine, respectively, attached to an activated heterocyclic ring. The Pictet-Spengler condensation of the three substrates with aldehydes led to the synthesis of novel N-rich polyheterocyclic system hitherto not reported. Our modified strategy opens up possibilities to design novel substrates with aryl amines linked via C or N to either deactivated or activated heterocyclic privileged structure, which in turn can be used for the synthesis of novel fused polyheterocyclic skeletons. (c) 2008 Elsevier Ltd. All rights reserved.