Beilstein J. Org. Chem.2021,17, 1499–1502, doi:10.3762/bjoc.17.106
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
a valuable route to mono- and disubstituted imidazoles.
Keywords: Asmic; cyclization; imidazoles; isocyanides; nitriles; Introduction
The imidazole core is the seventh most prevalent heterocycle among nitrogen-containing pharmaceuticals [1]. The privileged efficacy of imidazoles emanates from the
contain an adjacent electron withdrawing group (1, R1 = EWG) [13]. Installation of an electron withdrawing group adjacent to an isocyanide facilitates the deprotonation but creates weak nucleophiles 2 that are insufficiently nucleophilic to react with nitriles [14]. Described below is the use of Asmic