Journal of Organic Chemistry 2013-02-01

Synthesis of phenanthridine derivatives by microwave-mediated cyclization of o-furyl(allylamino)arenes.

Matthew Lovell Read, Lise-Lotte Gundersen

Index: J. Org. Chem. 78(3) , 1311-6, (2013)

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Abstract

A novel and efficient synthesis of phenanthridines and aza analogues is reported. The key step is a microwave-mediated intramolecular Diels-Alder cyclization of o-furyl(allylamino)arenes. In the presence of a catalytic amount of acid, the DA-adduct reacts further to give the dihydrophenanthridines, which easily can be oxidized to fully aromatic compounds by air in the presence of UV light or by DDQ.