- Unusual Oxidation in Thionyl Chloride: Novel Synthesis of Methyl 3-alkoxy-1,4-dioxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylates
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Oxidation of methyl 1,4-dioxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 1 with thionyl chloride gives an unstable intermediate that reacts with alcohols to give 3-alkoxy-1,4-dioxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylates (e.g. 6) and that is reduced with N-acetylcysteine to regenerate 1.In this system thionyl chloride is a convenient alternative oxidant to lead tetraacetate for the preparation of these masked equivalents of the unusual and reactive dienophile methyl 1,4-dioxo-1,4-dihydroisoquinoline-3-carboxylate 7.
- Beattie, John F.,Hales, Neil J.
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p. 751 - 752
(2007/10/02)
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