Definition:
The a-addition of an iminium ion and the conjugate base of a carboxylic acid to an isocyanide, followed by spontaneous rearrangement of the a-adduct to yield an a-aminocarboxamide derivative.
Frequency of appearance:
This bar graph represents all of the online articles that were found to contain this specific name reaction in the title of the article. Tetrahedron letters, Tetrahedron, Synthetic letters, Synthesis, Journal of Organic Chemistry and Journal of the American Chemical Society are represented here. This table by no means represents the periodicity of the name reaction found in the literature.
Original reference:
- Ugi, Angew. Chem. Int. Ed. 1, 8 (1962).
Recent academic references: Click here for more references
- A New Resin-Bound Universal Isonitrile for the Ugi 4CC Reaction: Preparation and Applications to the Synthesis of 2,5-Diketopiperazines and 1,4-Benzodiazepine-2,5-diones
- Kennedy, A. L.; Fryer, A. M.; Josey, J. A.; Org. Lett.; 2002; 4(7); 1167-1170.
- Liquid-Phase Combinatorial Synthesis of Alicyclic Lactams via Ugi Four-Component Reaction
- Gedey, S.; Van der Eycken, J.; Fulop, F.; Org. Lett., 2002; 4(11); 1967-1969.
- An Efficient Synthesis of Morpholin-2-one Derivatives Using Glycolaldehyde Dimer by the Ugi Multicomponent Reaction
- Kim, Y. B., et al., Org. Lett; 2001; 3(26); 4149-4152.
Recent process references:
- Some Items of Interest to Process R&D Chemists and Engineers, Selected by the Editor
- Laird, T.; Org. Process Res. Dev.; 1998; 2(5); 282-286.
- Fast Scale-Up Using Solid-Phase Chemistry
- Raillard, S. P.; Ji, G.; Mann, A. D.; Baer, T. A.;
Org. Process Res. Dev.; (Article); 1999; 3(3); 177-183.
Mechanism: http://icg.harvard.edu/~chem117/files/L18/Lecture_18.ppt
Scope and Limitations:
Synonyms: