Synthesis of Hydroxyalkyl Heterocycles by Ring Transformation of Spiroepoxy Lactones with Binucleophiles

Abstract

Spiroepoxy lactones 2 and 3 were obtained by epoxidation of α-alkylidenelactones 1 with dimethyldioxirane. Reaction of spiroepoxy lactones 2 with binucleophiles gave access to a number of hydroxyalkyl heterocycles with interesting substituent patterns. Depending on both the kind of substituent at the oxirane ring as well as the type of the binucleophile, the spiroepoxy lactones react either as C₃ or as C₂ bielectrophilic building blocks giving 4-, 6- and 7-membered partially saturated N-and S-heterocycles 5, 6, 8, 9, 11 and 13.

Key words

epoxidations - ring transformation - thiazepinones - di­azepinones - 1,4-thiazinones - benzothiopyranones - β-lactams

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Full details have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-205880. Copies of the data can be obtained free of charge on apllication to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.