14750-19-7Relevant articles and documents
Reaction of ethyl acylindole-2-carboxylates with thallium trinitrate (synthetic studies on indoles and related compounds. XXXIII)
Tani,Matsumoto,Aida,Arikawa,Nakane,Yokoyama,Murakami
, p. 443 - 453 (1994)
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.
Synthesis of Quaternary 3,3-Disubstituted 2-Oxindoles from 2-Substituted Indole Using Selectfluor
Jiang, Xiaojian,Yang, Junjie,Zhang, Feng,Yu, Pei,Yi, Peng,Sun, Yewei,Wang, Yuqiang
supporting information, p. 3154 - 3157 (2016/07/13)
A facile method to construct quaternary 3,3-disubstituted 2-oxindole from 2-substituted indole without a catalyst in mild conditions is developed. A mechanistic study suggests that an iminium-intermediate-triggered 1,2-rearrangement is involved, and a tra