Metal-Free Insertion Reactions of Diazo Carbonyls to Azlactones

Author(s)

Amarante, Giovanni W. ^[4]

Affiliation

^[1] Univ Fed Juiz de Fora, Dept Chem, BR-36036900 Juiz De Fora, MG - Brazil

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. 83, n. 18, p. 11399-11406, SEP 21 2018.
• Web of Science Citations: 1

Abstract

Insertion reactions of diazo carbonyls to azlactones in basic conditions have been performed. The developed method allows the preparation of a wide range of oxazole derivatives in yields ranging from 74 to 98%. Different substituents on both azlactone rings and diazo carbonyls do not compromise the methodology, even those containing stereogenic centers. Isotopic labeling experiments revealed the mechanism may proceed through a rare diazo carbonyl activation by an ammonium salt derivative. (AU)

• FAPESP's process: 17/23329-9 - Synthesis of substituted cyclopentanes and long chain polyols from abundant chemical platforms derived from biomass
• Grantee: Antonio Carlos Bender Burtoloso
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/18009-4 - Molecular design, synthesis and trypanocidal activity of cruzain reversible covalent inhibitors
• Grantee: Carlos Alberto Montanari
• Support Opportunities: Research Projects - Thematic Grants