To present the synthesis and reactivity of the most important classes of heterocyclic compounds and to present case studies drawn from major drug classes.

By the end of the module students will have achieved a solid foundation in Organic Chemistry.

In particular they will be expected to be able to demonstrate a clear understanding of

• The structural features and reactivity of heterocyclic compounds, including stereochemistry.
• Some of the major synthetic pathways in heterocyclic chemistry, involving carbon-carbon and carbon-heteroatom bond formation, functional group interconversions and ring substitution.
• Awareness of the importance of heterocylcles as key components in major drug classes and combinatorial libraries.

In addition they will be able to give examples of their use in modern synthetic methodology and have an awareness of the importance of three-dimensional structure in Organic Chemistry.

Lecture -

Tutorial -

Lectures 1 and 2: Revision of the reactivity of 5 and 6-membered monoheterocyclic aromatic systems (pyrroles, furans, thiophenes and pyridines). Stereoelectronics of ring closing reactions. Baldwin’s rules. The concept of “Chemical Space.”

Aromatic heterocyclic chemistry: Synthesis (8  lectures)

Lecture 3, 4 and 5: The synthesis and reactivity of pyridines, quinolines and isoquinolines with relevant examples of medicinally important compounds containing these heterocyclic units.

Lectures 6, 7 and 8: The synthesis and reactivity of diazoles such as imidazoles, pyrazoles, thiazole, triazoles and tetrazoles. Examples of the synthesis of pharmacologically active compounds containing these ring systems will be included.

Lectures 9 and 10: Synthesis  and reactivity of indoles. Examples of medicinally important compounds containing this heterocyclic unit will be included.

Saturated heterocyclic chemistry (4 lectures)

Lecture 11: Introduction to satu rated nitrogen and oxygen heterocycles including pyrrolidines, piperidines and tetrahydofurans.