Chemical and Pharmaceutical Bulletin p. 443 - 453 (1994)
Update date:2022-08-11
Topics:
Tani
Matsumoto
Aida
Arikawa
Nakane
Yokoyama
Murakami
Ethyl acylindole-2-carboxylates were treated with thallium trinitrate (TTN) in methanol, methyl orthoformate, methyl orthoformate/sulfuric acid, and acetic acid. The reactions in the former three methanolic solvents gave methyl indoleacetate derivatives via the Favorskii-type rearrangement reaction at the acyl group, whereas the reaction in acetic acid gave oxindole derivative with rearrangement of the C2-ethoxycarbonyl group. The TTN reaction was applied to a model compound leading to the synthesis of lysergic acid.
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