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Indolenine Oxides, VIII. Reaction of 5,7‐di‐ tert ‐butyl‐3,3‐dimethyl‐3 H ‐indole 1‐Oxide with Grignard Reagents. – A New Stable Aminyl Oxide (Nitroxide)
Author(s) -
Döpp Dietrich,
Greci Lucedio,
NourelDin Ahmed Moukhtar
Publication year - 1983
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19831160602
Subject(s) - chemistry , reagent , solvent , indole test , oxide , grignard reaction , medicinal chemistry , grignard reagent , nitrone , organic chemistry , catalysis , cycloaddition
The title compound 1 , unsubstituted at C‐2, is efficiently converted into its 2‐substituted derivatives 4a , b by Grignard addition and lead dioxide oxidation. 4a , when subjected to the same sequence, gives high yields of the aminyl oxide 5a which is also formed in small amounts in the conversion of 1 together with two other minor compounds. The course of the reaction is influenced by the presence of a bulky tert ‐butyl group at C‐7 in 1 and by the solvent used for the Grignard reaction.