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Synthetic route to 4‐(2‐aminoethyl)‐5‐hydroxyindole derivatives
Author(s) -
Can Joseph G.,
Roufos Ioannis
Publication year - 1990
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.5570270744
Subject(s) - chemistry , claisen rearrangement , acetaldehyde , oxidative cleavage , indole test , carroll rearrangement , derivative (finance) , combinatorial chemistry , organic chemistry , stereochemistry , ethanol , catalysis , financial economics , economics
In synthetic studies leading to the title compounds, application of the Claisen rearrangement of 5‐allyloxyindole was investigated. Almost quantitative yields of Claisen rearrangement product were realized, and a strategy for oxidative cleavage of the allyl double bond to an indole‐4‐acetaldehyde derivative was developed. A new method for conversion of 2,3‐dihydroindoles into indoles was utilized: air oxidation in a strongly basic environment. The Claisen rearrangement of allyloxyindoles is presented as a method having considerable potential utility in synthesis of a variety of polysubstituted indoles.