Fischer indolisation of 2,6-dialkyl and 2,4,6-trialkylphenylhydrazones of diketones and ketoesters
2003; Elsevier BV; Volume: 44; Issue: 30 Linguagem: Inglês
10.1016/s0040-4039(03)01364-9
ISSN1873-3581
AutoresShambabu Joseph Maddirala, Vidya S. Gokak, Sharanabasava B. Rajur, L. D. Basanagoudar,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoUnlike the migration of a methyl group observed in the ZnCl2 or acetic acid-catalysed indolisation of phenylhydrazones, dry ethanolic HCl catalysed indolisation of 2,6-dimethyl- and 2,4,6-trimethylphenylhydrazones of various substituted butane-2,3-diones and ethyl pyruvates yields 7-methyl- and 5,7-dimethyl-3-substituted indoles indicating elimination of an ortho-methyl group during indolisation.
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