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A facile access to indigodianiles
Author(s) -
Kühn Christiane,
Beckert Rainer,
Friedrich Manfred,
Görls Helmar
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430621
Subject(s) - chemistry , benzotriazole , oxalic acid , lithium (medication) , combinatorial chemistry , indigo , cascade , organic chemistry , medicine , art , visual arts , endocrinology , chromatography
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.