A facile access to indigodianiles

✍ Scribed by Christiane Kühn; Rainer Beckert; Manfred Friedrich; Helmar Görls

• Book ID: 102338220
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2006
• Tongue: English
• Weight: 379 KB
• Volume: 43
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570430621

✦ Synopsis

Abstract

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Bis‐imidoylchlorides derived from oxalic acid can easily be transformed into the corresponding bis‐imino benzotriazoles. The fact that benzotriazole is a well‐established leaving group has been exploited for an improved synthesis of indigodianiles. Employing metallic lithium, the benzotriazoles can be converted in a cascade reaction into indigo bis‐arylimines in yields up to 45%. Formation of the reduced form of dimeric isocyanides is suggested as a key step.