Английская Википедия:Debus–Radziszewski imidazole synthesis

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Шаблон:Reactionbox 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 Шаблон:Ill.[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

Шаблон:Reflist

  1. Ebel, K., Koehler, H., Gamer, A. O., & Jäckh, R. "Imidazole and Derivatives." In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, Шаблон:Doi
  2. Шаблон:Cite journal
  3. 3,0 3,1 Шаблон:Cite journal
  4. Шаблон:Cite journal
  5. Шаблон:Cite journal
  6. 6,0 6,1 Шаблон:Cite journal