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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Gallo, Rafael D. C. [1] ; Campovilla, Jr., Orlando C. [1] ; Ahmad, Anees [1] ; Burtoloso, Antonio C. B. [1]
Total Authors: 4
[1] Univ Sao Paub, Inst Quim Sao Carlos, Sao Carlos, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: FRONTIERS IN CHEMISTRY; v. 7, FEB 8 2019.
Web of Science Citations: 1

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: 15/20084-0 - Total Synthesis of (-)-Brussonol, (+)-Komaroviquinona and its analogs targeting potential candidates with trypanocidal activity
Grantee:Anees Ahmad
Support type: Scholarships in Brazil - Post-Doctorate
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 type: 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 type: Research Projects - Thematic Grants