APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS .14. SYNTHETIC STRATEGIES BASED ON AROMATIC METALATION - A CONCISE REGIOSPECIFIC CONVERSION OF BENZOIC-ACIDS INTO THEIR ORTHO-PYRIDOYL DERIVATIVES

Authors
EPSZTAJN J JOZWIAK A KRYSIAK JA
Citation
J. Epsztajn et al., APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS .14. SYNTHETIC STRATEGIES BASED ON AROMATIC METALATION - A CONCISE REGIOSPECIFIC CONVERSION OF BENZOIC-ACIDS INTO THEIR ORTHO-PYRIDOYL DERIVATIVES, Tetrahedron, 50(9), 1994, pp. 2907-2916
Citations number
41
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
9
Year of publication
1994
Pages
2907 - 2916
Database
ISI
SICI code
0040-4020(1994)50:9<2907:AOOARR>2.0.ZU;2-0
Abstract
The synthesis of the 3-hydroxy-3-pyridyl-isoindolin-1-ones (5) and (6) via metallation (n-BuLi) of the benzanilides (1), and then the reacti on of the generated bis lithiated anilides (2) N,N-dimethylamides or m ethyl esters of pyridinecarboxylic acids (benzoylation reagents), and subsequent acidic hydrolysis of (5) and (6) as a way (general syntheti c strategy) of regiospecific transformation of benzoic acids into thei r ortho-benzoylated derivatives, is described.