8-FLUORO-6-(METHOXYMETHOXY)QUINOLINE - SYNTHESIS AND REGIOSELECTIVE FUNCTIONALIZATION VIA REACTION WITH ORGANOLITHIUM COMPOUNDS

Authors
STADLWIESER J BARBIER P TAYLOR S
Citation
J. Stadlwieser et al., 8-FLUORO-6-(METHOXYMETHOXY)QUINOLINE - SYNTHESIS AND REGIOSELECTIVE FUNCTIONALIZATION VIA REACTION WITH ORGANOLITHIUM COMPOUNDS, Helvetica Chimica Acta, 81(6), 1998, pp. 1088-1094
Citations number
11
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
81
Issue
6
Year of publication
1998
Pages
1088 - 1094
Database
ISI
SICI code
0018-019X(1998)81:6<1088:8-SARF>2.0.ZU;2-S
Abstract
8-Fluoro-6-(methoxymethoxy)quinoline (1) was synthesized, and the reac tivity of 1 against organolithium compounds was studied under differen t reaction conditions. With BuLi, directed ortho-metalation (DoM) was accompanied by 1,2-addition to the C=N bond. 1,2-Addition was exclusiv ely observed with t-BuLi. Selective ortho-metalation was achieved with MeLi (Table). Based on these findings, a short and high-yielding synt hesis of the highly functionalized quinolines 12a-c was developed.