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Synthesis of ortho ‐substituted aminopyridines. Metalation of pivaloylamino derivatives
Author(s) -
Estel L.,
Linard F.,
Marsais F.,
Godard A.,
Quéguiner G.
Publication year - 1989
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.5570260119
Subject(s) - chemistry , metalation , electrophile , pyridine , aminopyridines , ether , diethyl ether , organic chemistry , medicinal chemistry , catalysis
The three isomeric pivaloylaminopyridines were lithiated in more than 80% yields. Aminopyridine derivatives were treated by 2.5‐3 equivalents of the complex BuLi‐TMEDA at −10° in diethyl ether. Reaction of the lithiated species with various electrophiles afforded a number of ortho ‐substituted pivaloylaminopyridines in good yields. Secondary pyridine alcohols were oxidized to the corresponding aminopyridyl ketones. Pyridopyrimidines, benzonaphthyridines as well as an analogue of the natural antitumor alkaloid ellipticine has been synthesized showing the versatility of the method.