4 years ago

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

Oxidative Deaminations and Deisatinylations of Ugi-Azide and Ugi-3CR Products: A Two-Step MCR-Oxidation Protocol toward Functionalized α-Ketoamides and α-Ketotetrazoles
Christopher Hulme, Arthur Shaw, Christopher Foley
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00710

DOI: 10.1021/acs.orglett.7b00710

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