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IBX-mediated oxidative Ugi-type multicomponent reactions: application to the N and C1 functionalization of tetrahydroisoquinoline

An Ugi-type reaction of tetrahydroisoquinoline with an isocyanide and a carboxylic acid in the presence of iodoxybenzoic acid (IBX) afforded the 1,2-diacylated adduct in good to excellent yields. E.g., in the presence of IBX, reaction of 1,2,3,4-tetrahydroisoquinoline, PhCO2H, and BnNC gave 87% 2-benzoyl-N-benzyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamide (I). [on SciFinder (R)]

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