Studies on Benzodiazepinooxazoles. IV. The Formation of Quinolones by the Ring Contraction of a Benzo [6, 7]-1, 4-diazepino [5, 4-b]-oxazole Derivative

Abstract

Treatment of 10-chloro-2, 3, 5, 6, 7, 11b-hexahydro-7-methyl-11b-phenylbenzo [6, 7]-1, 4-diazepino [5, 4-b] oxazol-6-one (IV) with sodium hydride in dimethyl acetamide gave the two compounds, 6-chloro-3-(2-hydroxyethyl)-1-methyl-4-phenyl-2 (1H)-quinolone (V) and 6-chloro-3-hydroxy-1-methyl-4-pherryl-2 (1H)-quinolone (VI). A mechanistic assumption for the formation of V was discussed.