One-step synthesis of imidazoles from Asmic (anisylsulfanylmethyl isocyanide)

• DOI: 10.3762/bjoc.17.106
• Publication Date: 2021-06-24T11:49:51Z
• Authors: Louis G Mueller; Allen Chao; Embarek AlWedi; Fraser F Fleming
• Keywords: Imidazole; Imine; Conjugate

Substituted imidazoles are readily prepared by condensing the versatile isocyanide Asmic, anisylsulfanylmethylisocyanide, with nitrogenous π-electrophiles. Deprotonating Asmic lithium hexamethyldisilazide effectively generates a potent nucleophile that efficiently intercepts nitrile and imine electrophiles to afford imidazoles. In situ cyclization imidazole is promoted conjugate acid, hexamethyldisilazane, which facilitates requisite series of proton transfers. The rapid formation interchange anisylsulfanyl for hydrogen Raney nickel make method valuable route mono- disubstituted