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Aza-Riley Oxidation of Ugi-Azide and Ugi-3CR Products toward Vicinal Tricarbonyl Amides: Two-Step MCR-Oxidation Methodology Accessing Functionalized ?,?-Diketoamides and ?,?-Diketotetrazoles.

ABSTRACT: Direct oxidative deamination of glyoxal-derived Ugi-azide and Ugi three-component reaction products readily affords vicinal tricarbonyls (?,?-diketoamides) and ?,?-diketotetrazoles with two diversity elements. This significant extension of our previously described multicomponent reaction-oxidative deamination methodology is proposed to proceed through a mechanistically distinct SeO2-mediated C-N oxidation derived from an active enol of ?-amino-?-ketone systems, effectively an aza-Riley oxidation. This methodology accesses diverse VTC systems from prototypical amines, glyoxaldehydes, and isocyanide building blocks in a mere two steps.

SUBMITTER: Foley C

PROVIDER: S-EPMC6424580 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Aza-Riley Oxidation of Ugi-Azide and Ugi-3CR Products toward Vicinal Tricarbonyl Amides: Two-Step MCR-Oxidation Methodology Accessing Functionalized α,β-Diketoamides and α,β-Diketotetrazoles.

Foley Christopher C Shaw Arthur A Hulme Christopher C

Organic letters 20180221 5

Direct oxidative deamination of glyoxal-derived Ugi-azide and Ugi three-component reaction products readily affords vicinal tricarbonyls (α,β-diketoamides) and α,β-diketotetrazoles with two diversity elements. This significant extension of our previously described multicomponent reaction-oxidative deamination methodology is proposed to proceed through a mechanistically distinct SeO<sub>2</sub>-mediated C-N oxidation derived from an active enol of α-amino-β-ketone systems, effectively an aza-Rile ...[more]

PMID: 29466017

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