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Synlett 2004(1): 182-186  
DOI: 10.1055/s-2003-43346
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Pyridinophane with endo-Annular Donor Sites

Katie Campbella, Natasha M. Tiemstraa, Natasha S. Prepas-Strobecka, Robert McDonaldb, Michael J. Fergusonb, Rik R. Tykwinski*a
a Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada
b X-ray Crystallography Laboratory, Department of Chemistry, University of Alberta, Canada
Fax: +1(780)4928231; e-Mail: rik.tykwinski@ualberta.ca;
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Publication History

Received 16 September 2003
Publication Date:
26 November 2003 (online)

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Abstract

Our synthetic efforts toward the realization of cross-conjugated macrocycles containing 2,6-diethynylpyridine sub-units are described. Macrocycle 4b was efficiently constructed from easily accessible building blocks using a series of palladium-catalyzed cross-coupling and copper-catalyzed homocoupling reactions. The synthesis, characterization and solid state characteristics of this macrocycle, as well as its precursors are provided in the discussion that follows.

Key words

alkynes - cross-conjugation - cross-coupling - homocoupling - macrocycles - pyridines