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8‐Fluoro‐6‐(methoxymethoxy)quinoline: Synthesis and regioselective functionalization via reaction with organolithium compounds
Author(s) -
Stadlwieser Josef,
Barbier Pierre,
Taylor Sven
Publication year - 1998
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19980810522
Subject(s) - metalation , chemistry , organolithium compounds , regioselectivity , quinoline , surface modification , reactivity (psychology) , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine , ion , alternative medicine , pathology , deprotonation
8‐Fluoro‐6‐(methoxymethoxy)quinoline ( 1 ) was synthesized, and the reactivity of 1 against organolithium compounds was studied under different reaction conditions. With BuLi, directed ortho ‐metalation (DoM) was accompanied by 1,2‐addition to the CN bond. 1,2‐Addition was exclusively observed with t ‐BuLi. Selective ortho‐metalation was achieved with MeLi ( Table ). Based on these findings, a short and high‐yielding synthesis of the highly functionalized quinolines 12a – c was developed.