Synthesis of Oxazinanones: Intramolecular Cyclization of Amino Acid-Derived Diazoketones via Silica-Supported HClO4 Catalysis.
Front Chem, 2019;7:62.
Gallo RDC[1], Campovilla OC Jr[1], Ahmad A[1], Burtoloso ACB[1]
Affiliations
PMID: 30800653DOI: 10.3389/fchem.2019.00062
Impact factor: 5.545
Abstract
A Brønsted acid catalyzed intramolecular cyclization of N-Cbz-protected diazoketones, derived from α-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.
Keywords: Brønsted acid; diazo carbonyls; heterocycles; intramolecular cyclization; oxazinanones
More resources
Full text:
Europe PubMed Central; PubMed Central
EndNote: Download