923276-76-0Relevant articles and documents
Unusual sterically controlled regioselective lithiation of 3-bromo-5-(4,4′-dimethyl)oxazolinylpyridine. Straightforward access to highly substituted nicotinic acid derivatives
Robert, Nicolas,Bonneau, Anne-Laure,Hoarau, Christophe,Marsais, Francis
, p. 6071 - 6074 (2006)
(Chemical Equation Presented) Lithiation of 5-bromonicotinic acid protected as secondary or tertiary amide as well as (4,4′-dimethyl)oxazoline with lithium amides is reported. The unusual C-2 and C-4 regioselective lithiation of 3-bromo-5-(4,4′-dimethyl)oxazolinylpyridine using LTMP versus LDA was observed, providing a new route to substituted nicotinic acid scaffolds. The methodology was applied to the synthesis of novel C-4 and C-6 arylated 5-bromonicotinic acids.