| Ugi reaction | |
|---|---|
| Named after | Ivar Karl Ugi |
| Reaction type | Coupling reaction |
| Identifiers | |
| Organic Chemistry Portal | ugi-reaction |
| RSC ontology ID | RXNO:0000129 |
In organic chemistry, the Ugi reaction is a multi-component reaction involving a ketone or aldehyde, an amine, an isocyanide and a carboxylic acid to form a bis-amide.[1][2][3][4] The reaction is named after Ivar Karl Ugi, who first reported this reaction in 1959.
The Ugi reaction is exothermic and usually complete within minutes of adding the isocyanide. High concentration (0.5M - 2.0M) of reactants give the highest yields. Polar, aprotic solvents, like DMF, work well. However, methanol and ethanol have also been used successfully. This uncatalyzed reaction has an inherent high atom economy as only a molecule of water is lost, and the chemical yield in general is high. Several reviews have been published.[5][6][7][8][9][10][11][12]‹The template Excessive citations inline is being considered for deletion.› [excessive citations]
Due to the reaction products being potential protein mimetics there have been many attempts to development an enantioselective Ugi reaction,[13] the first successful report of which was in 2018.[14]
- ^ Ugi I, Meyr R, Fetzer U, Steinbrückner C (1959). "Versuche mit Isonitrilen". Angew. Chem. 71 (11): 386. doi:10.1002/ange.19590711110.
- ^ Ugi I, Steinbrückner C (1960). "Über ein neues Kondensations-Prinzip". Angew. Chem. 72 (7–8): 267–268. Bibcode:1960AngCh..72..267U. doi:10.1002/ange.19600720709.
- ^ Ugi, I. (1962). "The α-Addition of Immonium Ions and Anions to Isonitriles Accompanied by Secondary Reactions". Angewandte Chemie International Edition in English. 1 (1): 8–21. doi:10.1002/anie.196200081.
- ^ Boltjes A, Liu H, Liu H, Dömling A (2017). "Ugi Multicomponent Reaction". Org. Synth. 94: 54–65. doi:10.15227/orgsyn.094.0054.
- ^ Tripolitsiotis, Nikolaos P.; Thomaidi, Maria; Neochoritis, Constantinos G. (2020-11-15). "The Ugi Three-Component Reaction; a Valuable Tool in Modern Organic Synthesis". European Journal of Organic Chemistry. 2020 (42): 6525–6554. doi:10.1002/ejoc.202001157. ISSN 1434-193X. S2CID 224890321.
- ^ Ugi I, Lohberger S, Karl R (1991). "The Passerini and Ugi Reactions". Comprehensive Organic Synthesis. Vol. 2. Oxford: Pergamon. pp. 1083–1109. ISBN 0-08-040593-2.
- ^ Ugi I, Werner B, Dömling A (2003). "The Chemistry of Isocyanides, their MultiComponent Reactions and their Libraries" (PDF). Molecules. 8: 53–66. doi:10.3390/80100053. S2CID 53949436.
- ^ Banfi L, Riva R (2005). "The Passerini Reaction". In Overman LE (ed.). Organic Reactions. Vol. 65. Wiley. ISBN 0-471-68260-8.)
- ^ Tempest PA (November 2005). "Recent advances in heterocycle generation using the efficient Ugi multiple-component condensation reaction". Current Opinion in Drug Discovery & Development. 8 (6): 776–88. PMID 16312152.
- ^ Ugi I, Heck S (February 2001). "The multicomponent reactions and their libraries for natural and preparative chemistry". Combinatorial Chemistry & High Throughput Screening. 4 (1): 1–34. doi:10.2174/1386207013331291. PMID 11281825.
- ^ Bienayme H, Hulme C, Oddon G, Schmitt P (September 2000). "Maximizing synthetic efficiency: multi-component transformations lead the way". Chemistry: A European Journal. 6 (18): 3321–9. doi:10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-A. PMID 11039522.
- ^ Dömling A, Ugi I (September 2000). "Multicomponent Reactions with Isocyanides". Angewandte Chemie. 39 (18): 3168–3210. Bibcode:2000AngCh..39.3168D. doi:10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U. PMID 11028061.
- ^ Wang Q, Wang DX, Wang MX, Zhu J (May 2018). "Still Unconquered: Enantioselective Passerini and Ugi Multicomponent Reactions". Accounts of Chemical Research. 51 (5): 1290–1300. doi:10.1021/acs.accounts.8b00105. PMID 29708723.
- ^ Zhang J, Yu P, Li SY, Sun H, Xiang SH, Wang JJ, et al. (September 2018). "Asymmetric phosphoric acid-catalyzed four-component Ugi reaction". Science. 361 (6407): eaas8707. doi:10.1126/science.aas8707. PMID 30213886.