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Synthesis 1994; 1994(1): 87-92
DOI: 10.1055/s-1994-25411
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Substituted Dipyridylethenes and -ethynes and Key Pyridine Building Blocks

Paul-Michael Windscheif* , Fritz Vögtle
  • *Institut für Organische Chemie and Biochemie der Universität Bonn, Gerhard-Domagk-Straße 1, D-53121 Bonn 1, Germany
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Publication History

Publication Date:
17 September 2002 (online)

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Various new 2,5-disubstituted pyridines were prepared. The 2-substituted 5-formylpyridines 8, 15a-b were obtained by reduction of the nicotinic acid 3, hydrolysis of the bis(morpholino)methylpyridine 6 or the reaction of 5-bromopyridines 12 and 14 with lithium butoxide in DMF. Dipyridylethenes 16a-b,e were synthesized by Wadsworth-Emmons reaction with pyridyl phosphonate 7 or by coupling of the aldehydes by McMurry reaction to the ethenes 16c-d. After bromination of the C=C double bond of the dipyridylethenes 16a-d, dipyridylacetylenes 18a-d were obtained via elimination of the 1,2-dipyridyl-1,2-dibromoethanes 17a-d.