A synthetic approach to 2,3,4-substituted pyridines useful as scaffolds for tripeptidomimetics |
| |
Authors: | Stina Saitton Jan Kihlberg Kristina Luthman |
| |
Institution: | a Department of Chemistry, Medicinal Chemistry, Göteborg University, SE-412 96 Göteborg, Sweden b Department of Chemistry, Organic Chemistry, Umeå University, SE-901 87 Umeå, Sweden |
| |
Abstract: | 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. |
| |
Keywords: | Peptidomimetic Pyridine Scaffold Grignard reaction Halogen-dance |
本文献已被 ScienceDirect 等数据库收录! |
|