ChemFiles 2006, 6.6, 3.

Aldehydes are perennially attractive building blocks due to their ability to easily react with many nucleophiles. Recent work by Kiselyov describes a one-pot procedure to polysubstituted pyrimidines using various aldehydes (Scheme 1).1

one-pot procedure to polysubstituted pyrimidines

Scheme 1

Collman has used 1-methylimidazole-5-carboxaldehyde in the synthesis of a functionalized tripodal ligand, which can serve as CuB site mimics of cytochrome c oxidase (Scheme 2).2 More recently, 1-methylimidazole-5-carboxaldehyde has been used in the synthesis of a series of tetrahydroquinoline analogues that show potent antimalarial activity (Scheme 3).3 Smith has used 1-methylpyrazole-4-carboxaldehyde to synthesize a series of orally active inhibitors of lipoprotein-associated phospholipase A2 (Scheme 4).4

functionalized tripodal ligand

Scheme 2

tetrahydroquinoline analogues

Scheme 3

lipoprotein-associated phospholipase A2

Scheme 4

Highly substituted 2-amino-4,6-dichloropyrimidine-5-carboxaldehyde has been of recent interest as well. One recent communication describes its use in the synthesis of an unnatural amino acid (ATPC) with promise in peptidomimetics.5 Another report uses 2-amino-4,6-dichloropyrimidine-5-carboxaldehyde as a key building block in the synthesis of a crucial tricyclic intermediate for a series of new A3 adenosine antagonists (Scheme 5).6

A3 adenosine antagonists

Scheme 5


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  1. Kiselyov, A. S. Tetrahedron Lett. 2005, 46, 1663.
  2. Collman, J. P. et al. J. Org. Chem. 2001, 66, 8252.
  3. Nallan, L. et al. J. Med. Chem. 2005, 48, 3704.
  4. Boyd, H. F. et al. Bioorg. Med. Chem. Lett. 2002, 12, 51.
  5. Bissyris, E. E. et al. Synthesis 2005, 3159.
  6. Baraldi, P. G. et al. Bioorg. Med. Chem. 2003, 11, 4161.

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