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N ‐Substituted 1‐Aminoindoles from Electrogenerated N ‐Substituted 2‐( ortho ‐Nitrosophenyl)ethylamines
Author(s) -
FrontanaUribe B. A.,
Moinet C.,
Toupet L.
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199902)1999:2<419::aid-ejoc419>3.0.co;2-v
Subject(s) - chemistry , aqueous solution , medicinal chemistry , intramolecular force , electrochemistry , alkyl , redox , aqueous medium , aryl , combinatorial chemistry , stereochemistry , organic chemistry , electrode
An electrochemical methodology offering efficient access to N ‐alkyl‐ and N ‐aryl‐substituted 1‐aminoindoles has been developed. N ‐Substituted 2‐( ortho ‐nitrosophenyl)ethylamines, electrogenerated in a “redox” flow cell, undergo intramolecular cyclization to hydrocinnoline‐type intermediates. Under slightly basic conditions, these undergo spontaneous ring‐contraction to produce the N ‐substituted heterocycles in good yields. The reactions have been studied in slightly acidic and slightly basic aqueous alcoholic media.