Réaction multicomposants

Une réaction multicomposants (RMC ou MCR de l'anglais multicomponent reaction) est une réaction chimique qui met en jeu au moins trois réactifs. Elle permet ainsi de synthétiser en une étape (en « one-pot ») des molécules souvent complexes à partir de petites molécules[1].

Exemples

Principal réactif Réaction Découvreur Date de la découverte Nombre de réactifs Sigle : initial du nom - nombre de réactif et CR pour component reaction Produits formés
Composé carbonylé Réaction de Strecker[2] Adolph Strecker 1850 3 Acides aminés
Réaction de Hantzsch[3] Arthur Rudolf Hantzsch 1881 3 Dihydropyridines
Réaction de Biginelli[4] Pietro Biginelli 1891 3 Dihydropyrimidinones
Réaction de Mannich[5] Carl Mannich (en) 1912 3 Composés β-aminocarbonylés, aussi appelés base de Mannich (en)
Réaction de Bucherer-Bergs[6],[7] Hans Theodor Bucherer et Hermann Bergs 1934 3 B-3CR Hydantoïnes
Réaction d'Asinger[8] Friedrich Asinger (en) 1956 4 A-4CR Thiazolines
Isonitrile Réaction de Passerini[9] Mario Passerini 1921 3 α-acyloxy amide
Réaction de Ugi[10] Ivar Karl Ugi 1959 4 U-4CR Bis-amide

Avantages

Les réactions multicomposants évitent de passer par plusieurs étapes pour obtenir un produit, ce qui minimise le temps de manipulation et les risques de perte de produits lors des étapes intermédiaires.

Liens externes

Références

  1. ↑ Xavier Bataille et Erwan Beauvineau, Synthèse parallèle basée sur la réaction multicomposants de Biginelli Une approche de la chimie verte, l’actualité chimique, mai 2009, n° 330
  2. ↑ (de) A. Strecker, « Ueber die künstliche Bildung der Milchsäure und einen neuen, dem Glycocoll homologen Körper », Liebigs Annalen Chem., vol. 75, no 1,‎ , p. 27–45 (ISSN 0075-4617, DOI 10.1002/jlac.18500750103)
  3. ↑ Hantzsch, A., « Condensationprodukte aus Aldehydammoniak und Ketonartigen Verbindungen », Chemische Berichte, vol. 14, no 2,‎ , p. 1637–8 (DOI 10.1002/cber.18810140214)
  4. ↑ (de) P. Biginelli, Chemische Berichte, 1891, 24, 1317 & 2962.
  5. ↑ C. Mannich et W. Krösche, « Ueber ein Kondensationsprodukt aus Formaldehyd, Ammoniak und Antipyrin », Archiv der Pharmazie, vol. 250,‎ , p. 647–667 (DOI 10.1002/ardp.19122500151)
  6. ↑ (de) H. T. Bucherer et W. Steiner, « On reactions of α-oxy-nitriles and α-amino-nitriles - Synthesis of hydantoins », Journal für praktische Chemie, vol. 140, nos 10/12,‎ , p. 291-316 (ISSN 0941-1216)
  7. ↑ Bergs, H. Ger. pat. 566,094 (1929)
  8. ↑ (de) F. Asinger, « Über die gemeinsame Einwirkung von Schwefel und Ammoniak auf Ketone », Angewandte Chemie, vol. 68, no 12,‎ , p. 413 (ISSN 1433-7851, DOI 10.1002/ange.19560681209)
  9. ↑ Passerini, M.; Simone, L. Gazz. Chim. Ital. 1921, 51, 126–29
  10. ↑ Ugi, I; Meyr, R.; Fetzer, U.; Steinbrückner, C., « Versuche mit Isonitrilen », Angewandte Chemie, vol. 71, no 11,‎ , p. 386 (DOI 10.1002/ange.19590711110)
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