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Common synthetic reactions of imidazole

2019-03-12 来源:亚科官网

Imidazole is an important intermediate in organic synthesis. Many drugs contain this structure, such as the antifungal drugs ketoconazole, miconazole, clotrimazole, etc. The following is a summary of the common synthetic reaction of imidazole.

1Debus-Radziszewski imidazole synthesis reaction

A three-component condensation of 1,2-dicarbonyl compound, ammonia and aldehyde give an imidazole reaction. The most commonly used dicarbonyl compound is glyoxal, and 1,2-diketone or aldehyde ketone can also be reacted to synthesize various imidazoles.

2Wallach imidazole synthesis reaction

The reaction of synthesizing 1,2-dialkylimidazole by a N-alkylamide containing a β-nitrogen atom or an α-diamide in phosphorus pentachloride or phosphorus oxychloride. The most commonly used substrate for this reaction is N,N-dialkyloxamide, which is used as a substrate to give 1,2-dialkyl-5-chloroimidazole. This method has certain limitations, but when the alkyl carbon chain is long or the steric hindrance is large, the cyclization rate is low.

3Bredereck imidazole synthesis

The condensation of α-diketone (or α-hydroxyketone, α-amino ketone, α-mercapto ketone) and formylamide gives the reaction of imidazole.

4. Kaiser-Johnson-Middleton dinitrile cyclization reaction

Under the action of HBr, the dinitrile is used to synthesize a bromine-substituted five-, six- or seven-membered ring heterocyclic ring.

5. Gröbcke-Blackburn-Bienaymé Aminoimidazole Synthesis Reaction

A one-pot condensation of an aldehyde, an isonitrile and 2-aminopyridine, 2-aminopyrimidine, 2-aminopyrazine or 2-aminothiophene, etc., containing a H2N-C=N structural compound gives an aminoimidazole. This reaction is a multi-component reaction with a mechanism similar to the Ugi reaction.

6Van Leusen imidazole synthesis reaction

The reaction of aldimine and p-toluenesulfonylmethyl isocyanide (TosMIC) to form an imidazole under basic conditions. Since the activity of the imine is much higher than that of the aldehyde, the reaction is later extended to a three-component reaction (VL-3CR) which is directly closed to the TosMIC one-pot method after directly reacting the aldehyde with an amine to obtain an imine.

Related links: Imidazole

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