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
| Autor: | Arthur Y. Shaw, Christopher Foley, Christopher Hulme |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Azides
Isocyanide Two step Deamination Tetrazoles 010402 general chemistry 01 natural sciences Biochemistry Article chemistry.chemical_compound Selenium Oxides Molecule Physical and Theoretical Chemistry Amines Aldehydes Cyanides Molecular Structure 010405 organic chemistry Organic Chemistry Temperature Oxidative deamination Ketones Enol Combinatorial chemistry Amides 0104 chemical sciences chemistry Alcohols Azide Oxidation-Reduction Vicinal |
| Popis: | 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(2)-mediated C–N oxidation derived from an active enol of α-amino-β-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. |
| Databáze: | OpenAIRE |
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