Synthesen von Heterocyclen, CCIV1 Reaktionen mit cyclischen Oxalylverbindungen, XIX2 Eine einfache Synthese von 5-Benzoyl-6-phenyl-1.3-dioxin-4-onen / Syntheses of Heterocycles, CCIV1 Reactions of Cyclic Oxalyl Compounds, XIX 2 A Simple Synthesis of 5 Benzoyl-6-phenyl-1,3-dioxin-4-ones

Abstract

4-Benzoyl-5-phenyl-2,3-dihydrofuran-2,3-dione (1) reacts with aldehydes or ketones via the acylketene-intermediate (2) yielding the 1,3-dioxin-4-ones (3). The aldehyde derivatives (3 a-e) can be converted into the anilino-chalcone (5) or the anilino acrylic acid (6) by treating with aniline at 20 °C. 6 and diazomethane combine to the acrylic acid methyl ester (7), which by heating (200 °C) is cyclisized to the quinolin-4-ole (8). On the other hand, the keto derivatives 3f-h and aniline give the dibenzoyl acetic acid anilide (9).