Ugi reaction

The Ugi reaction is a multi-component reaction in organic chemistry involving a ketone or aldehyde, an amine, an isocyanide and a carboxylic acid to form a bis-amide.The reaction is named after Ivar Karl Ugi, who first published this reaction in 1962.

Mechanism

1 / Imine formation with amine versus ketone

2/ Proton exchange

3/ Nucleophilic addition of the isocyanide

4/ Nuclephilic addition of the carboxylic acid anion

5/ Mumm rearrangement

Patents References

References

Synthesis of 5- and 6-membered lactams via solvent-free microwave Ugi reaction

Tetrahedron Letters: Article in Press, Accepted Manuscript

 

Proline-like β-turn mimics accessed via Ugi reaction involving monoprotected hydrazines 

Tetrahedron Letters Volume 51, Issue 10, 10 March 2010, Pages 1367-1370. 

 

Ugi reaction for the synthesis of 4-aminopiperidine-4-carboxylic acid derivatives. Application to the synthesis of carfentanil and remifentanil
Tetrahedron Letters Volume 51, Issue 22, 2 June 2010, Pages 2983-2985

 

Isonitriles from the Baylis–Hillman adducts of acrylates: viable precursor to tetrazolo-fused diazepinones via post-Ugi cyclization
Tetrahedron Letters Volume 51, Issue 3, 20 January 2010, Pages 510-516

 

Highly Efficient Oxidation of Amines to Imines by Singlet Oxygen and Its Application in Ugi-Type Reactions

 Org. Lett.200911 (20), pp 4568–4571


 Ugi Reactions with Ammonia Offer Rapid Access to a Wide Range of 5-Aminothiazole and Oxazole Derivatives

J. Org. Chem.200974 (18), pp 7084–7093

 

Application of the Ugi Reaction for the One-Pot Synthesis of Uracil Polyoxin C Analogues

J. Org. Chem.200974 (13), pp 4870–4873


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