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A synthetic approach to 2,3,4-substituted pyridines useful as scaffolds for tripeptidomimetics
Umeå University, Faculty of Science and Technology, Chemistry.
Umeå University, Faculty of Science and Technology, Chemistry.
2004 (English)In: Tetrahedron, ISSN 0040-4020, Vol. 60, no 29, 6113-20 p.Article in journal (Refereed) Published
Abstract [en]

The synthesis of 2,3,4-substituted pyridine derivatives useful as scaffolds in the development of peptidomimetics is described. The use of a variety of electrophiles in a halogen-dance reaction to produce 3-alkyl-2-fluoro-4-iodo-pyridine derivatives as ‘functionalized scaffolds’ and the possibility to differentiate between the reactivities of the two halogen handles have been explored. Coupling of amino acid derivatives in the 4-position of the pyridine was found to proceed efficiently by conversion of iodo-pyridine to a Grignard derivative, which was allowed to react with a protected amino aldehyde. Substitution of fluorine in the 2-position of the pyridine was found to be facile with alkoxide nucleophiles, whereas amines were much less reactive.

Place, publisher, year, edition, pages
2004. Vol. 60, no 29, 6113-20 p.
Keyword [en]
peptidomimetic, pyridine, scaffold, Grignard reaction, halogen-dance
Identifiers
URN: urn:nbn:se:umu:diva-14232DOI: doi:10.1016/j.tet.2004.05.048OAI: oai:DiVA.org:umu-14232DiVA: diva2:153903
Available from: 2007-05-24 Created: 2007-05-24 Last updated: 2011-01-12Bibliographically approved

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