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Note | Regular issue | Vol 51, No. 9, 1999, pp.2159-2162
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8577
Chemo- and Regioselective Nucleophilic Reactions of (Bromomethyl)methylmaleic Anhydride: Synthesis of α-Quinoxalinyl- and α-Benzothiazinylacrylic Acids

Anil M. Deshpande, Arvind A. Natu, and Narshinha P. Argade*

*Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India


The (bromomethyl)methylmaleic anhydride (2) on reaction with o-phenylenediamine and o-aminothiophenol underwent chemo- and regioselective ring opening followed by intramolecular Michael type addition and 1,4-elimination reactions to furnish kinetically controlled products α-quinoxalinylacrylic acid (5) and α-benzothiazinylacrylic acid (6) in good yields.