Hofmann-Type Elimination in the Efficient N-Alkylation of Azoles: Imidazole and Benzimidazole

András Horváth

doi:10.1055/s-1994-25414

Synthesis 1994; 1994(1): 102-106
DOI: 10.1055/s-1994-25414

paper

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Hofmann-Type Elimination in the Efficient N-Alkylation of Azoles: Imidazole and Benzimidazole

András Horváth^*

^*Alkaloida Chemical Company Ltd., H-4440 Tiszavasvári, Hungary

Abstract

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A simple and efficient preparation of 1-substituted 1H-azoles (imidazole and benzimidazole) has been developed, which involves a selective Hofmann-type elimination of the 2-cyanoethyl group from the azolium salts obtained by the reaction of halides with 1H-imidazole-1-propanenitrile and 1H-benzimidazole-1-propanenitrile. Overall yields of 1-substituted 1H-azoles decreased in the order: primary alkyl halides ≥ allylhalides ≥ secondary alkyl halides > benzyl halides > α-keto halides, in relation to the alkylating agent, and imidazole > benzimidazole, in relation to the azole, respectively.

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