Debus–Radziszewski imidazole synthesis

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Debus–Radziszewski imidazole synthesis
Named after ]
Reaction type Ring forming reaction

The Debus–Radziszewski imidazole synthesis is 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

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