Aldehydes

Aldrich ChemFiles 2006, 6.6, 3.

Aldrich 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

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

Scheme 2

Scheme 3

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

Scheme 5

Sigma-Aldrich is pleased to add these and other new aldehydes to our expanding collection.

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Materials

     

References

  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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