From Hydrazones to N-Anilinoindoles
Savelii V Barkovskii1, Konstantin A Lyssenko1, Mikhail S Nechaev1,2
1Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russia Federation.
None:
The Suzuki reaction with 4,4-dichoro-1,2-diaza-but-1,3-dienes opened access to doubly arylated diazadienes prepared in up to 95% yield. It was found that treatment of 4,4-diaryl-1,2-diaza-butenes with acid results in 100% selective intramolecular cyclization to form 1-anilino-2,3-diaryliindoles in up to 99% yield. A broad reaction scope was demonstrated. The mechanism of the reaction was studied by using quantum chemical computations. The reactivity of 1-anilino-2,3-diphenyliindole was investigated to reveal the high synthetic utility of these heterocycles.
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