8‐Fluoro‐6‐(methoxymethoxy)quinoline: Synthesis and regioselective functionalization  via  reaction with organolithium compounds | Zendy

Stadlwieser Josef | Zendy; Barbier Pierre | Zendy; Taylor Sven | Zendy

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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.

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