Issue 15, 1995

New synthesis of carboxin and oxycarboxin pesticides: application to the preparation of their new analogues substituted at the C-2 methyl group

Abstract

A new synthesis of carboxin 1a and its 4,4-dioxide derivative, oxycarboxin 2a, has been devised via N-bromosuccinimide-promoted oxidative rearrangement of acetoacetanilide 1,3-oxathiolane 3. The replacement of N-bromosuccinimide with molecular bromine leads to the formation, from compound 3, of a C-2 bromomethylcarboxin derivative 1b. The latter is conveniently exploited to prepare a new class of carboxins and oxycarboxins (after oxidation of the sulfur) substituted at the C-2 methyl, by replacement of the bromine atom with various nucleophiles.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1995, 1971-1973

New synthesis of carboxin and oxycarboxin pesticides: application to the preparation of their new analogues substituted at the C-2 methyl group

R. Caputo, C. Ferreri, A. Guaragna, G. Palumbo and S. Pedatella, J. Chem. Soc., Perkin Trans. 1, 1995, 1971 DOI: 10.1039/P19950001971

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