Synthesis of N,N-Disubstituted 1-Aryl-1,3-dihydro-2H-isoindole-2-carbothioamides
摘要:
A convenient method for the synthesis of N,N-disubstituted 1-aryl-1,3-dihydro-2H-isoindole-2-carbothioamides starting from 2-[aryl(methoxy)methyl]phenyl bromides is described. Thus, the reaction of 1-[aryl(methoxy)methyl]-2-(isothiocyanatomethyl)benzenes, derived from the starting materials by an easily operated five-step sequence under mild conditions, with secondary amines provides the corresponding thiourea derivatives, which cyclize on treatment with methanesulfonic acid to afford the desired products.
A ligand-controlled palladium-catalyzed three-component reaction of o-bromobenzaldehyde, N-tosylhydrazone, and methanol is described. This reaction uses readily available compounds as starting materials while displaying a broad substrate scope and good functional group compatibility.