12. 1,2-Azoles and 1,3-Azoles

  1. John A. Joule1 and
  2. Keith Mills2

Published Online: 6 AUG 2012

DOI: 10.1002/9781118380208.ch12

Heterocyclic Chemistry at a Glance, Second Edition

Heterocyclic Chemistry at a Glance, Second Edition

How to Cite

Joule, J. A. and Mills, K. (2012) 1,2-Azoles and 1,3-Azoles, in Heterocyclic Chemistry at a Glance, Second Edition, John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/9781118380208.ch12

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



  • 1,2-azoles and 1,3-azoles;
  • chemical reactions of azoles;
  • electrophilic addition to N;
  • azoles, reacting with acids forming azolium salts;
  • imidazole and pyrazole N-alkylation;
  • imidazole and pyrazole alkylations;
  • alkylate the N-anion of the heterocycles;
  • nucleophilic substitution of halogen;
  • 1,3-azolium ylides;
  • 1,3-azoles ring synthesis, disconnections


This chapter contains sections titled:

  • Introduction

  • Electrophilic addition to N

  • Electrophilic substitution at C

  • Nucleophilic substitution of halogen

  • N-Deprotonation and N-metallated imidazoles and pyrazoles

  • C-Metallated N-substituted imidazoles and pyrazoles, and C-metallated thiazoles and isothiazoles

  • C-Deprotonation of oxazoles and isoxazoles

  • Palladium(0)-catalysed reactions

  • 1,3-Azolium ylides

  • Reductions

  • Pericyclic reactions

  • Oxygen and amine substituents

  • 1,3-Azoles ring synthesis – disconnections

  • Synthesis of thiazoles and imidazoles from α-halo-ketones

  • Synthesis of 1,3-azoles from 1,4-dicarbonyl compounds

  • Synthesis of 1,3-azoles using tosylmethyl isocyanide

  • Synthesis of 1,3-azoles via dehydrogenation

  • 1,2-Azoles ring synthesis – disconnections

  • Synthesis of pyrazoles and isoxazoles from 1,3-dicarbonyl compounds

  • Synthesis of isoxazoles and pyrazoles from alkynes

  • Synthesis of isothiazoles from β-amino α, β-unsaturated carbonyl compounds

  • Exercises