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Lithiations and Magnesiations on Quinoline and Isoquinoline

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Metalation of Azines and Diazines

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 31))

Abstract

Recent advances in the formation of lithiated or magnesiated quinolines and isoquinolines by deprotonative metalation and halogen–metal exchange are summarized and discussed. Subsequent trappings with electrophiles show that both methods are efficient to generate functionalized building blocks, which are of foremost importance in supramolecular chemistry, material science, or in the synthesis of biologically active compounds.

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Abbreviations

BuLi:

n-Butyllithium

dba:

Dibenzylidene acetone

DEE:

Diethyl ether

DMA:

Dimethylacetamide

DMAE:

N,N-Dimethylaminoethoxide

DMF:

Dimethylformamide

LDA:

Lithium diisopropylamide

LTMP:

Lithium 2,2,6,6-tetramethylpiperidide

LUMO:

Lowest unoccupied molecular orbital

MesLi:

Mesityllithium

MOM:

Methoxymethyl

NFSI:

N-Fluorobenzenesulfonimide

Py:

Pyridyl

s-BuLi:

sec-Butyllithium

t-BuLi:

tert-Butyllithium

Tf:

Triflate

THF:

Tetrahydrofuran

TMEDA:

N,N,N′,N′-Tetramethylethylenediamine

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Acknowledgment

The Institut Universitaire de France is gratefully acknowledged.

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Authors and Affiliations

  1. Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS - Université de Rennes 1, Equipe Chimie et Photonique Moléculaires, Bâtiment 10A, Case 1003, Campus Scientifique de Beaulieu, 35042, Rennes, France

    Floris Chevallier & Florence Mongin

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  1. Floris Chevallier
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Correspondence to Florence Mongin .

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Editors and Affiliations

  1. Vienna University of Technology Institute of Applied Synthetic Chemistry, Vienna, Austria

    Michael Schnürch

  2. Vienna University of Technology Institute of Applied Synthetic Chemistry, Vienna, Austria

    Marko D. Mihovilovic

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Chevallier, F., Mongin, F. (2012). Lithiations and Magnesiations on Quinoline and Isoquinoline. In: Schnürch, M., Mihovilovic, M. (eds) Metalation of Azines and Diazines. Topics in Heterocyclic Chemistry, vol 31. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2012_92

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