Multi-component named reaction in organic chemistry
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
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][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. 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.
In organic chemistry, the Ugireaction is a multi-component reaction involving a ketone or aldehyde, an amine, an isocyanide and a carboxylic acid to form...
Ugi or UGI may refer to: Ugireaction, in chemistriy UGI Corporation, an American energy company Ugi Island in the Solomon Islands Camillo Ugi (1884–1970)...
isoimide group to an imide. The reaction is of relevance as part of the Ugireaction. Mumm, O. (1910). "Umsetzung von Säureimidchloriden mit Salzen organischer...
N-dimethylformamide, exhibit low solubility in water. Amides undergo many chemical reactions, although they are less reactive than esters. Amides hydrolyse in hot...
in many multicomponent reactions of interest in organic synthesis, two of which are: the Ugireaction and the Passerini reaction. Isocyanides also participate...
chemistry. He is known for the research on multicomponent reactions, yielding the Ugireaction. After he went to Germany from Estonia in 1941 he began his...
synthesis of an unnatural analogue was reported featuring an interrupted Ugireaction as the key step. Scalable and modular total synthesis of the natural...
California, San Diego. Chemistry (2008). New convertible isocyanides for the Ugireaction; application to the stereoselective synthesis of omuralide. p. 11....
of Retosiban 8 the linear peptide 5 is formed by the four-component Ugireaction of the carboxybenzyl (Cbz) protected R-indanylglycine 1, D-alloisoleucine...
the Ugireaction to assist in the formation of the pentacyclic core. This reaction was unprecedented for using such a one pot multicomponent reaction in...
S-methylated endothiopeptide. The endothiopeptide was obtained by a thio-Ugireaction. The resulting macrocycle was obtained as a racemic mixture at the amidine...
Submeta and Nature. As well as concentrating on compounds related to the Ugireaction, the ONSchallenge allows anyone to request a solubility measurement experiment...
of Epelsiban 11, the linear peptide 8 is formed by the four-component Ugireaction of the carboxybenzyl (Cbz) protected R-indanylglycine 4, D-alloisoleucine...
variations of Josiphos ligands have been reported. One family is prepared from Ugi's amine. An important improvement on initial syntheses has been using N(CH3)2...
amines to isoquinolines, the Schmidt reaction with ketones, and the Ugi, Ritter, Pinner and Passerini reactions. IUPAC Gold Book: nitrilium ions Clayden...
McGouran, J. F.; Leung, I. K. H.; Berridge, G. (2013). "The Ugi four-component reaction enables expedient synthesis and comparison of photoaffinity probes"...
the hospital forced the evacuation of 20 people. Two schools in Marika and Ugi were completely destroyed. Fissures and landslides were also seen in the...
for $8.3 billion, SAP's most expensive purchase to that date. Analysts' reactions to the purchase were mixed, with Thomas Becker of Commerzbank questioning...
Mayr [de], Johann Mulzer, Hans-Ulrich Reissig, Jürgen Sauer [de] and Ivar Karl Ugi. His daughter, mathematician Birge Huisgen-Zimmermann, was born in 1946....
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