5. Pyridines

  1. John A. Joule1 and
  2. Keith Mills2

Published Online: 6 AUG 2012

DOI: 10.1002/9781118380208.ch5

Heterocyclic Chemistry at a Glance, Second Edition

Heterocyclic Chemistry at a Glance, Second Edition

How to Cite

Joule, J. A. and Mills, K. (2012) Pyridines, in Heterocyclic Chemistry at a Glance, Second Edition, John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/9781118380208.ch5

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



  • pyridines;
  • simple pyridines, electrophilic addition to nitrogen;
  • electrophilic substitution at carbon, in mesomeric transfer;
  • electrophilic substitution regiochemistry;
  • Friedel–Crafts alkylation/acylation for carbon substituents;
  • pyridine nitrogen and metal centres, in coordination chemistry;
  • nucleophilic substitutions of hydrogen;
  • nucleophilic addition to pyridinium salts;
  • pyridines, role in electrocyclic processes;
  • pyridine N-oxides, and ambiphilic nature


This chapter contains sections titled:

  • Electrophilic addition to nitrogen

  • Electrophilic substitution at carbon

  • Nucleophilic substitution

  • Nucleophilic addition to pyridinium salts

  • C-metallated pyridines

  • Palladium(0)-catalysed reactions

  • Oxidation and reduction

  • Pericyclic reactions

  • Alkyl and carboxylic acid substituents

  • Oxygen substituents

  • N-Oxides

  • Amine substituents

  • Ring synthesis – disconnections

  • Synthesis of pyridines from 1,5-dicarbonyl compounds

  • Synthesis of pyridines from an aldehyde, two equivalents of a 1,3-dicarbonyl compound and ammonia

  • Synthesis of pyridines from 1,3-dicarbonyl compounds and a C2N unit

  • Exercises