Synthesis of Oxazinanones: Intramolecular Cyclization of Amino Acid-Derived Diazoketones via Silica-Supported HClO4 Catalysis

Author(s)

Gallo, Rafael D. C. ; Campovilla, Orlando C., Jr. ; Ahmad, Anees ; Burtoloso, Antonio C. B.

• Document type: Journal article
• Source: RONTIERS IN CHEMISTR; v. 7, p. 7-pg., 2019-02-08.

Abstract

A Bronsted acid catalyzed intramolecular cyclization of N-Cbz-protected diazoketones, derived from alpha-amino acids, is described. The reaction proceeds under metal-free conditions and is promoted by ecofriendly silica-supported HClO4 as the catalyst and methanol as the solvent. This transformation enables the short synthesis of various 1 ,3-oxazinane-2,5-diones under mild reaction conditions and in good yields (up to 90%). The set-up is very simple; by just mixing all reagents together with no work-up necessary before purification, this protocol takes a greener approach. (AU)

• 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
• FAPESP's process: 15/20084-0 - Total Synthesis of (-)-Brussonol, (+)-Komaroviquinona and its analogs targeting potential candidates with trypanocidal activity
• Grantee: Anees Ahmad
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• 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