Oxidative Deaminations and Deisatinylations of Ugi-Azide and Ugi-3CR Products: A Two-Step MCR-Oxidation Protocol toward Functionalized α‑Ketoamides and α‑Ketotetrazoles

A new
postcondensation multicomponent reaction (MCR) methodology,
comprising oxidative deaminations enabling access to multiple privileged
carbonyl-containing scaffolds in two steps, is described. These protocols
allow facile access to functionalized α-ketoamide and α-ketotetrazole
small-molecule peptidomimetic-like building blocks from prototypical
synthons with two points of diversity. Incorporation of chalcone and
alkynyl moieties with further ring-forming reactions enables access
to additional novel heterocyclic ring systems, including a unique
and potentially highly pharmacologically relevant scaffold, a 1,2-selenazol-3­(2H)-one.