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

中文翻译：

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从 Asmic（苯硫基甲基异氰化物）一步合成咪唑

通过将多功能异氰化物 Asmic、茴香硫基甲基异氰化物与含氮 π-亲电试剂缩合，可以很容易地制备取代的咪唑。用六甲基二硅肼锂去质子化 Asmic 可以有效地产生一种有效的亲核试剂，可以有效地拦截腈和亚胺的亲电试剂以提供咪唑。共轭酸六甲基二硅氮烷促进了咪唑的原位环化，这促进了必要的一系列质子转移。咪唑的快速形成以及茴香硫基与雷尼镍的氢交换使该方法成为获得单和二取代咪唑的有价值的途径。