SYNTHESIS OF POLYFUNCTIONALIZED AZEPINONES

The azepinones 2 and 5 have been synthesized via ring expansion of the dioxopyrrolidine derivative 1 with dimethylacetylene dicarboxylate or methyl propiolate, respectively, in basic medium (NaH). Acid hydrolys is of 2 gave furo [3,4-c]azepinetetrone 6 whereas alkaline gave furo[3 ,4-c]azepinetrione 7. Bromination of 6 with N-bromosuccinimide yielded the derivative 8. Compound 6 was treated with methyl orthoformate to afford the derivative 9, which was condensed with benzylamine to pyrro lo[3,4-c]azepinetrione derivative 10.