Some reactions of β-ketoesters derived from 9,10-phenanthraquinone with ammonia, hydrazine, and substituted hydrazines

Abstract

A number of β-ketoesters based on cyclopentanone, with and without additional αβ′-unsaturation, have been prepared from 9,10-phenanthraquinone and ethyl or methyl acetoacetate. Reactions of these with ammonia, hydrazine, and substituted hydrazines involve variously attack at the ester, the keto-group, and/or the olefinic group; ring-opening sometimes occurs, as does new ring-closure. Several novel compounds are described, including a 1,2-diazatriphenylene which is readily converted into a dibenzocinnolone.