Synthesis

Synthesis of Unsymmetrical Pyrrolo [3, 2-b] pyrrole-2, 5-diones and Bis (quinazolin-4-on-2-yls) by Double-Anion-Capture Reactions of Unsymmetrical Oxaldi ( …

F Helmholz, R Schroeder, P Langer

Index: Helmholz, Falko; Schroeder, Rita; Langer, Peter Synthesis, 2006 , # 15 p. 2507 - 2514

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Citation Number: 9

Abstract

The reaction of ethyl 2-chloro-2-oxoacetate with a number of anilines 1 gave the known [12] ethyl 2-oxo-2-(arylamino)acetates 2 (Scheme [1] ). The reaction of 2 with a variety of anilines afforded the unsymmetrical oxalamides 3a-j (42-83%). Reflux of a toluene solution of oxalamides 3 with phosphorus pentachloride furnished, after recrystallisation from n-heptane, the unsymmetrical oxalic acid bis(imidoyl) dichlorides 4a-j (23-77%). The lithium diisopropylamide mediated ...