Chemistry of sulfonylmethyl isocyanides. 12. Base-induced cycloaddition of sulfonylmethyl isocyanides to carbon,nitrogen double bonds. Synthesis of 1,5-disubstituted and 1,4,5-trisubstituted imidazoles from aldimines and imidoyl chlorides

Albert M. Van Leusen*, Jurjen Wildeman, Otto H. Oldenziel

*Department of Organic Chemistry, Groningen University, Nijenborgh 16, 9747 AG Groningen, The Netherlands

A. M. Van Leusen, J. Wildeman, O. H. Oldenziel, J. Org. Chem., 1977, 42, 1153-1159.

DOI: 10.1021/jo00427a012

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Abstract

Base-induced cycloaddition of tosylmethyl isocyanide (TosMIC) to aldimines in protic medium occurs with subsequent elimination of p-toluenesulfinic acid to give the otherwise difficulty accessible 1,4-disubstituted imidazoles. Addition of TosMIC to imidoyl chlorides is accompanied by the loss of HCl, and leads to 1,4,5-trisubstituted imidazoles.

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Key Words

Van Leusen Imidazole Synthesis, Imidazoles

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ID: J42-Y1977-0200