Organic Chemistry Portal



Reaction of 1,3-Bis(het)arylmonothio-1,3-diketones with Sodium Azide: Regioselective Synthesis of 3,5-Bis(het)arylisoxazoles via Intramolecular N-O Bond Formation

Mary Antony P, Gantala L. Balaji, Pethaperumal Iniyavan and Hiriyakkanavar Ila*

*New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur, Bangalore 560064, India, Email:

M. A. P, G. L. Balaji, P. Iniyavan, H. Ila, J. Org. Chem., 2020, 85, 15422-15436.

DOI: 10.1021/acs.joc.0c02216

see article for more reactions


An efficient reaction of 1,3-bis(het)arylmonothio-1,3-diketones with sodium azide provides 3,5-bis(het)arylisoxazoles in high yields at room temperature in the presence of IBX as catalyst. The reaction is applicable to a broad range of substrates. The reaction of β-ketodithioesters with sodium azide furnishes β-ketonitriles in good yields.

see article for more examples

Key Words

isoxazoles, organocatalysis

ID: J42-Y2020