7. Quinolines and Isoquinolines

  1. John A. Joule1 and
  2. Keith Mills2

Published Online: 6 AUG 2012

DOI: 10.1002/9781118380208.ch7

Heterocyclic Chemistry at a Glance, Second Edition

Heterocyclic Chemistry at a Glance, Second Edition

How to Cite

Joule, J. A. and Mills, K. (2012) Quinolines and Isoquinolines, in Heterocyclic Chemistry at a Glance, Second Edition, John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/9781118380208.ch7

Author Information

  1. 1

    The School of Chemistry, The University of Manchester, UK

  2. 2

    Independent Consultant, UK

Publication History

  1. Published Online: 6 AUG 2012
  2. Published Print: 4 SEP 2012

ISBN Information

Print ISBN: 9780470971222

Online ISBN: 9781118380208

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Keywords:

  • quinolines and isoquinolines;
  • electrophilic addition to nitrogen;
  • quinoline and isoquinoline, benzene rings and pyridine rings;
  • electrophilic substitution, of benzene compounds;
  • substitution of leaving groups;
  • nucleophilic addition to quinolinium/isoquinolinium salts;
  • quinoline/isoquinoline with acid chloride, ‘Reissert compounds’;
  • boronic acid and stannane derivatives, in cross-coupling;
  • alkyl substituents, quinoline-2- and 4-alkyl, isoquinoline 1-position;
  • ring synthesis, quinoline/isoquinoline considered separately

Summary

This chapter contains sections titled:

  • Electrophilic addition to nitrogen

  • Electrophilic substitution at carbon

  • Nucleophilic substitution

  • Nucleophilic addition to quinolinium/isoquinolinium salts

  • C-Metallated quinolines and isoquinolines

  • Palladium(0)-catalysed reactions

  • Oxidation and reduction

  • Alkyl substituents

  • Oxygen substituents

  • N-Oxides

  • Ring synthesis – disconnections

  • Synthesis of quinolines from anilines

  • Synthesis of quinolines from ortho-aminoaryl ketones or aldehydes

  • Synthesis of isoquinolines from 2-arylethamines

  • Synthesis of isoquinolines from aryl-aldehydes and an aminoacetaldehyde acetal

  • Synthesis of isoquinolines from ortho-alkynyl aryl-aldehydes or corresponding imines

  • Exercises