Debus–Radziszewski imidazole synthesis

In today's world, Debus–Radziszewski imidazole synthesis is a highly relevant topic that has captured the attention of millions of people around the world. With a significant impact on various aspects of daily life, Debus–Radziszewski imidazole synthesis has been the subject of debate and discussion in all spheres of society. From its impact on health and well-being, to its influence on economics and politics, Debus–Radziszewski imidazole synthesis has become a point of interest and concern for many. In this article, we will explore the phenomenon of Debus–Radziszewski imidazole synthesis in depth, analyzing its implications and consequences in different contexts. With a global perspective, we seek to shed light on this topic and provide a broader and more complete vision of its scope and importance in today's world.

Debus–Radziszewski imidazole synthesis
Named after Heinrich Debus
Bronisław Leonard Radziszewski
Reaction type Ring forming reaction

The Debus–Radziszewski imidazole synthesis is a multi-component reaction used for the synthesis of imidazoles from a 1,2-dicarbonyl, an aldehyde, and ammonia or a primary amine. The method is used commercially to produce several imidazoles.[1] The process is an example of a multicomponent reaction.

The reaction can be viewed as occurring in two stages. In the first stage, the dicarbonyl and two ammonia molecules condense with the two carbonyl groups to give a diimine:

Debus-Radziszewski imidazole synthesis part I

In the second stage, this diimine condenses with the aldehyde:

Debus-Radziszewski imidazole synthesis part I

However, the actual reaction mechanism is not certain.[2][3]

This reaction is named after Heinrich Debus[4] and Bronisław Leonard Radziszewski.[5][6]

A modification of this general method, where one equivalent of ammonia is replaced by an amine, affords N-substituted imidazoles in good yields.[3]

Arduengo imidazoles

This reaction has been applied to the synthesis of a range of 1,3-dialkylimidazolium ionic liquids by using various readily available alkylamines.[6]

References

  1. ^ Ebel, K., Koehler, H., Gamer, A. O., & Jäckh, R. "Imidazole and Derivatives." In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, doi:10.1002/14356007.a13_661
  2. ^ Crouch, R. David; Howard, Jessica L.; Zile, Jennifer L.; Barker, Kathryn H. (2006). "Microwave-Mediated Synthesis of Lophine: Developing a Mechanism To Explain a Product". J. Chem. Educ. 83 (11): 1658–1660. doi:10.1021/ed083p1658.
  3. ^ a b Gelens, E.; De Kanter, F. J. J.; Schmitz, R. F.; Sliedregt, L. A. J. M.; Van Steen, B. J.; Kruse, Chris G.; Leurs, R.; Groen, M. B.; Orru, R. V. A. (2006). "Efficient library synthesis of imidazoles using a multicomponent reaction and microwave irradiation". Molecular Diversity. 10 (1): 17–22. doi:10.1007/s11030-006-8695-3. PMID 16404525.
  4. ^ Debus, Heinrich (1858). "Ueber die Einwirkung des Ammoniaks auf Glyoxal". Justus Liebigs Annalen der Chemie. 107 (2): 199–208. doi:10.1002/jlac.18581070209.
  5. ^ Radzisewski, Br. (1882). "Ueber Glyoxalin und seine Homologe". Berichte der deutschen chemischen Gesellschaft. 15 (2): 2706–2708. doi:10.1002/cber.188201502245.
  6. ^ a b Damilano, Giacomo; Kalebić, Demian; Binnemans, Koen; Dehaen, Wim (2020). "One-pot synthesis of symmetric imidazolium ionic liquids N,N-disubstituted with long alkyl chains". RSC Adv. 10 (36): 21071–21081. doi:10.1039/D0RA03358H. PMC 9054310. PMID 35518762.