Module Details
The information contained in this module specification was correct at the time of publication but may be subject to change, either during the session because of unforeseen circumstances, or following review of the module at the end of the session. Queries about the module should be directed to the member of staff with responsibility for the module.
Title HETEROCYCLIC CHEMISTRY AND DRUG SYNTHESIS
Code CHEM338
Coordinator Dr IA O'Neil
Chemistry
Ion@liverpool.ac.uk
Year CATS Level Semester CATS Value
Session 2014-15 Level Three Second Semester 7.5

Aims

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


Learning Outcomes

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 mo dern synthetic methodology and have an awareness of the importance of three-dimensional structure in Organic Chemistry.


Syllabus
1  Aromatic heterocyclic chemistry: (2 lectures)

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 saturated nitrogen and oxygen heterocycles including pyrrolidines, piperidines and tetrahydofurans.

 

Lectures 12 and 13: The synthesis and reactivity of pyrrolidines and piperidines, which will include examples of medicinally important compounds containing these saturated heterocyclic units.

 

 

Lecture 14: The synthesis and reactivity of tetrahydrofurans.

 

 

 

 

Revision Lectures (2 lectures)

 

 

Lectures 15 and 16: Revision tutorials.

 

2 .

Teaching and Learning Strategies

Lectures

Tutorials

This module consists of 16 lectures (50 minutes) and 2 tutorials with assessment problems related to material presented in the lectures. The students are expected to spend 4 hours on these assessed problems.

The examination requires a solid foundation in Organic Chemistry, includes the major synthetic pathways introduced together with problems based on understanding of reactivity, and requires examples of synthetic methodology.

The tutorials provide opportunities for practice of the reaction mechanisms of the important carbon-carbon and carbon-heteroatom bond forming reactions and application to real-life drug molecules.


Teaching Schedule
  Lectures Seminars Tutorials Lab Practicals Fieldwork Placement Other TOTAL
Study Hours 16

   2

       18
Timetable (if known)              
Private Study 57
TOTAL HOURS 75

Assessment
EXAM Duration Timing
(Semester)		 % of
final
mark		 Resit/resubmission
opportunity		 Penalty for late
submission		 Notes
Unseen  1.5hrs  Semester 2  80  Yes  Standard UoL penalty applies   
CONTINUOUS Duration Timing
(Semester)		 % of
final
mark		 Resit/resubmission
opportunity		 Penalty for late
submission		 Notes
TBC  2x2 hrs problem sets  Semester 2  20  No reassessment opportunity  Standard UoL penalty applies  Continuous Assessment Two assessed problem based tutorial exercises of 10 % each. This work is not marked anonymously August resit for PGT students if applicable. Integrated Master's students resit at the next normal opportunity.  

Recommended Texts

Organic Chemistry, J. Clayden, N. Greeves, S. Warren and P. Wothers, OUP, 2000

 Additional Reading:

 “Top Drugs, Top Synthetic Routes”, by J. Saunders (OUP no. 90).

“Aromatic Heterocyclic Chemistry” by D.T. Davies; Oxford Science Publications, 1992.

“Bacteria and Antibacterial Agents” by J. Mann and J. C. Crabbe, Spektrum Academic Publishers, 1996.

“Heterocyclic Chemistry”, T. L. Gilchrist, 3rd. edition.

Advanced Reading: