Ugi Reaction

Aldrich ChemFiles 2006, 6.7, 3.

Aldrich ChemFiles 2006, 6.7, 3.

The Ugi reaction (Scheme 1) is an isonitrile-based MCR that provides a rapid route for the preparation of a-aminoacyl amide derivatives. The Ugi 4 component condensation of an amine, oxo compound, carboxylic acid and an isocyanide is the most documented and versatile MCR.

Scheme 1

Combined with combinatorial chemistry, Musonda et al. describe using the Ugi MCR to develop a library of novel compounds to screen against known antimalrial pharmacophores. The library consisted of aminoquinoline containing a-aminoacyl amides that were used in structure-activity relationship (SAR) studies. This approach allowed them to synthesize a number of compounds in very few reaction steps and screen them rapidly.1

The Ugi reaction can be coupled with a post condensation reaction to increase the number of possible pharmacologically important scaffolds. An example is the Heck reaction. Umkehrer et al. recently demonstrated that the Ugi/Heck combination works well for high-throughput combinatorial library production of indol- 2-ones having four points of diversity. This scaffold is of interest because it has shown biological effect as antitumor(1) and tyrosine kinase(2) inhibitor activity.2



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  1. Musonda, C. et al. Bioorg. Med. Chem. Lett. 2004, 14, 3901–3905.
  2. Umkehrer et al. Tertahedron Lett. 2006, 47, 2391–2393.

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