Heterocyclic Chemistry: Parts 2 and 3

Year 3, Semester 1
Dr Boa, C120b, a.n.boa@hull.ac.uk
Contents Overview
Part 2
1.
HETEROCYCLES - INTRODUCTION
2.
QUINOLINES & QUINOLONES
3.
ISOQUINOLINES
4.
INDOLES
5.
SELECTED REACTIONS OF HETEROCYCLES
Part 3
1.
1,3-DIPOLAR CYCLOADDITION REACTIONS - INTRODUCTION
2.
ISOXAZOLES AND ISOXAZOLINES
3.
ISOXAZOLIDINES
4.
DIAZOLES AND TRIAZOLES
COURSE REVIEW AND REVISION
Suggested reading

Organic Chemistry, J. Clayden, N. Greeves, S. Warren and P. Wothers, OUP. 1st

Ed., Chapters 42, 43 and 44 (sections thereof); 2nd Ed. Chapters 29, 30 and 34.
Aromatic Heterocyclic Chemistry, D.T. Davies, OUP, QD 400 D2
Heterocyclic Chemistry, T.L. Gilchrist, QD 400 G5
Heterocyclic Chemistry, J.A. Joule, K. Mills and G.F. Smith, QD 400 J8
Learning outcomes:
At the end of the course you should be able to:
1. Identify, draw and be familiar with the names of the classes of heterocyclic
molecules covered in the course (not detailed nomenclature)
2. Distinguish between cyclisation and cycloaddition reactions and describe the
general features of each class of reaction
3. Formulate products arising from cyclisation and cycloaddition reactions. I.e. work
out what heterocycle is produced from a given set of reagents (including methods
for making 1,3-dipoles)
4. Apply the ring modification reactions covered to given heterocycles
5. Give synthetic sequences for the syntheses covered (identify intermediates)
6. Describe the influence of reaction conditions on product (isomer) distribution
7. Explain isomer distribution in cyclisation reactions in terms of thermodynamic and
kinetic effects.
8. Describe the effect of ring substituents on rates of cyclisation reaction and isomer
distribution.
For a full set of notes and sample past paper questions (some with solutions) see
http://www.hull.ac.uk/php/chsanb/teaching.html