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 CHEM337
Coordinator Dr AV Stachulski
Chemistry
Year CATS Level Semester CATS Value
Session 2008-09 Level Three First 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 modern synthetic methodology and have an awareness of the importance of three-dimensional structure in Organic Chemistry.


Syllabus
0 

Topic

Aromatic heterocyclic chemistry: reactivity (4 lectures)

Lecture 1

Recap of the reactivity of 6-membered monoheterocyclic aromatic systems, especially pyridine. Electrophilic and nucleophilic substitution.

Lecture 2

Recap of the reactivity of 5-membered monoheterocyclic aromatic systems: pyrrole, furan and thiophene. Electrophilic and nucleophilic substitution.

Lecture 3

The reactivity of quinolines, isoquinolines treated as ben zopyridines, and diazines. Electrophilic and nucleophilic substitution.

Lecture 4

The reactivity of diazoles (imidazoles, pyrazoles), thiazoles, triazoles and tetrazoles.

Aromatic heterocyclic chemistry: synthesis (4 lectures)

Lecture 5

Synthesis of pyridines and pyrimidines.

Lecture 6

Synthesis of pyrroles, furans and thiophenes

Lecture 7

Synthesis of quinolines and isoquinolines.

Lecture 8

Synthesis of indoles and related benzo-fused systems.

Case studies: Heterocyclic Synthesis in Medicinal Chemistry (5 lectures)

Lecture 9

Calcium channel blockers (nifedipine, etc.)- dihydropyridine synthesis.

Lecture 10

Quinolone antibacterials and antimalarials, e. g. ciprofloxacin, chloroquine- quinoline synthesis

Lecture 11

Histamine antagonists (cimetidine, ranitidine)- imidazole and furan synthesis.

Lecture 12

 Beta-lactam antibiotics- penicillin and cephalosporin synthesis

Two tutorial sessions will complete the course


Teaching and Learning Strategies

This module consists of 16 lectures (50 minutes) and 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
Examination  1.5h  1st  80  August resit opportunity for Year 2 students only. see notes    Year 3 (and Year 4) students resit at the next normal opportunity. See "Teaching and Learning Strategies"  
CONTINUOUS Duration Timing
(Semester)		 % of
final
mark		 Resit/resubmission
opportunity		 Penalty for late
submission		 Notes
Continuous Assessment  4hrs  1st  20  No  Standard University Policy applies - see Department/School handbook for details.  Two assessed problem based tutorial of 10 % each. This work is not marked anonymously  

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: