Total Synthesis of Pyrrolnitrin. VI. Synthesis of Nitro-chloro-2-aminoacetophenones and 1-Aryl-1, 3-butanediones

Abstract

Synthetic methods of nitro-chloro-2-aminoacetophenones (XV) and 1-(nitro-chlorophenyl)-1, 3-butanediones (XXIII : R=H), starting materials for the synthesis of pyrrolnitrin (I) and its related compounds, were investigated. Neber rearrangement was shown to be suitable for the preparation of XV. Cleavage of ethyl 2-(nitro-chlorobenzoyl)-acetoacetate (XXI) and 2, 4-pentanedione (XXII) led to XXIII (R=H).