Synfacts 2006(6): 0554-0554  
DOI: 10.1055/s-2006-934467
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Imidazophenanthridinium Salts

Contributor(s): Victor Snieckus, Bärbel Wittel
A. D. C. Parenty, K. M. Guthrie, Y.-F. Song, L. V. Smith, E. Burkholder, L. Cronin*University of Glasgow, UK
Further Information

Publication History

Publication Date:
19 May 2006 (online)

Significance

The synthesis of a new class of heterocyclic aromatic cations by a new method is reported. The imidazophenanthridine intermediate, derived by an ammonolysis, cyclization, and oxidation sequence, is quaternized with a wide range of electrophiles to give the imidazophenanthridi­nium (IP) salts. The IP products show physical properties consistent with stable radical species. The X-ray crystal structure of imidazophenanthridine shows a π-π interaction in the solid state and an increased planarity with electron delocalization over the entire heterocylic framework.