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Paper | Regular issue | Vol 45, No. 1, 1997, pp.87-93
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7625
Synthesis of (Z)-3-Benzylidene-3,4-dihydro-2-oxo-2H-1,4-benzoxazine-5-carboxylic Acid, a Naturally Occurring Inhibitor of Glutathione S-Transferase

T. Ross Kelly,* Carmen Martinez, and Richard J. Mears

*E. F. Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02167, U.S.A.


Preparation of a number of 2H-1,4-benzoxazine-2-ones has been effected by reaction of substituted 2-aminophenols with methyl 3-phenylpyruvate. This methodology has been applied to afford a rapid and efficient synthesis of the naturally occuring glutathione S-transferase inhibitor (Z)-3-benzylidene-3,4-dihydro-2-oxo-2H-1,4-benzoxazine-5-carboxylic acid.