Synthesis 2013; 45(7): 893-895
DOI: 10.1055/s-0032-1318365
short paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Pyrido[3,4-c][1,9]phenanthroline – A Five-Step Procedure to a Novel N-Containing Ring Skeleton

Christopher Meier
Pharmaceutical Institute, Department of Pharmaceutical Chemistry, Christian Albrechts University of Kiel, Gutenbergstraße 76, 24118 Kiel, Germany   Fax: +49(431)8801352   Email: bclement@pharmazie.uni-kiel.de
,
Philip Sömmer
Pharmaceutical Institute, Department of Pharmaceutical Chemistry, Christian Albrechts University of Kiel, Gutenbergstraße 76, 24118 Kiel, Germany   Fax: +49(431)8801352   Email: bclement@pharmazie.uni-kiel.de
,
Ulrich Girreser
Pharmaceutical Institute, Department of Pharmaceutical Chemistry, Christian Albrechts University of Kiel, Gutenbergstraße 76, 24118 Kiel, Germany   Fax: +49(431)8801352   Email: bclement@pharmazie.uni-kiel.de
,
Bernd Clement*
Pharmaceutical Institute, Department of Pharmaceutical Chemistry, Christian Albrechts University of Kiel, Gutenbergstraße 76, 24118 Kiel, Germany   Fax: +49(431)8801352   Email: bclement@pharmazie.uni-kiel.de
› Author Affiliations
Further Information

Publication History

Received: 18 January 2013

Accepted after revision: 12 February 2013

Publication Date:
27 February 2013 (online)


Abstract

The condensation of paraformaldehyde with two equivalents of 4-methylpyridine-3-carbonitrile under basic conditions afforded 6-amino-11,12-dihydropyrido[3,4-c][1,9]phenanthroline, which was converted via the corresponding 6-oxo- and 6-chloro derivatives­ and a dehalogenation into 11,12-dihydropyrido[3,4-c][1,9]phenanthroline. The fully aromatized derivative pyrido[3,4-c][1,9]phenanthroline was obtained in an ultimate dehydrogenation procedure.

 
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