Synthesis 2014; 46(20): 2799-2807
DOI: 10.1055/s-0034-1378384
paper
© Georg Thieme Verlag Stuttgart · New York

Bimacrocyclic Pyridines and 1,8-Naphthyridines: Basicities and Application in Base Catalysis[1]

Timo Liebig
Otto-Diels-Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Olshausenstraße 40, 24098 Kiel, Germany   Fax: +49(431)8801558   Email: luening@oc.uni-kiel.de
,
Ulrich Lüning*
Otto-Diels-Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Olshausenstraße 40, 24098 Kiel, Germany   Fax: +49(431)8801558   Email: luening@oc.uni-kiel.de
› Author Affiliations
Further Information

Publication History

Received: 27 May 2014

Accepted after revision: 12 June 2014

Publication Date:
18 July 2014 (online)


Abstract

Di-α-substituted N-heterocycles such as 2,6-halogenopyridines or 2,7-dichloro-1,8-naphthyridines can be coupled with 2,6-bis(alkenyloxy) substituted areneboronic acids. The resulting tetraenes are then cyclized by ring-closing metathesis to give bimacrocyclic concave pyridines or concave 1,8-naphthyridines. The relative basicity of the concave N-heterocycles was measured and their activity and selectivity was tested in the base-catalyzed addition of alcohols to diphenylketene.

Supporting Information

 
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