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Heterocyclic Chemistry 1 Part 1 (06522)
Year 2, Semester 2
Dr Boa, C301, [email protected]
CONTENTS OVERVIEW Lecture 1: Synthesis of heterocycles from 1,4-dicarbonyl compounds
(furans, pyrroles, thiophenes and pyridazines) Lecture 2: Synthesis of heterocycles from 1,3-dicarbonyl compounds
(pyrroles, isoxazoles, pyrazoles and pyrimidines) Lecture 3: Synthesis of heterocycles from 1,5-dicarbonyl compounds (pyridines and dihydropyridines)
Suggested reading
Organic Chemistry, J. Clayden, N. Greeves, S. Warren and P. Wothers, Oxford University Press. Mainly Chapter 44.
Aromatic Heterocyclic Chemistry, D. T. Davies, (Oxford Primer No. 2): (QD 400 D2) useful in parts
More advanced texts: Heterocyclic Chemistry, 2nd Ed., T. L. Gilchrist and Heterocyclic Chemistry, 3rd Ed., J. A. Joules, K. Mills and G. F. Smith (QD 400 J8)
Learning outcomes:
At the end of the course you should be able to use reaction mechanisms to: 1. Paal-Knorr synthesis
Work out the furan, pyrrole or thiophene product arising from the reaction of 1,4-diketones in the Paal-Knorr reaction.
2. Knorr pyrrole synthesis Work out the product arising from a Knorr pyrrole synthesis. 3. Pyrazoles, isoxazoles and pyrimidines Work out the product(s) arising from the reaction of 1,3-diketones with (substituted)
hydrazines, hydroxylamine or amidines. 4. Pyridines
Work out the products arising from the reaction of 1,5-diketones with hydroxylamine.
5. Hantzsch pyridine synthesis Work out the products arising from a Hantzsch pyridine synthesis.
See http://www.hull.ac.uk/php/chsanb/teaching.html for a set of notes, past paper questions with solutions.
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