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 2021-22 Level 6 FHEQ Second Semester 7.5

Pre-requisites before taking this module (or general academic requirements):

 

Aims

The aim of the module is 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

(LO1) 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 heterocycles 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.


Teaching and Learning Strategies

This module consists of 16 lectures and two sets of assessment problems related to material presented in the lectures. The recorded lectures and detailed lecture notes will be published on Canvas at the rate of two per week, this is the same rate of delivery that has occurred in previous years. The lecture material will be enhanced by online tutorials in weeks 5 and 9.


Syllabus

 

* Introduction to heterocycles. Stereoelectronics of ring closing reactions. Baldwin's rules. The concept of "Chemical Space".
* Synthesis and reactions of pyridines and diazines. The synthesis of pyridine based drugs such as Omeprazole and Amlodipine.
* Chemistry of pyrroles, furans and thiopenes. The synthesis of drugs containing these ring sustems such as Losartan and Fatmotidine.
* Lipitor - A case study. This covers the detailed process of drug discovery.
* Chemistry of diazoles (imidazoles, pyrazoles, thiazoles, oxazoles) and the synthesis of drugs containing these ring systems
* Synthesis and reactivity of indoles. The synthesis of indole containing drugs as Sumatriptan
* Synthesis and chemistry of quinolones and isoquinolines, with relevant examples of medicinally important compounds containing these heterocyclic units including Norfloxacin, Ciprofloxacin, Quinapril and Paperavine.
* The synthesis of saturated nitrogen heterocycles including piperidines and pyrrolidines.


Recommended Texts

Reading lists are managed at readinglists.liverpool.ac.uk. Click here to access the reading lists for this module.

Teaching Schedule

  Lectures Seminars Tutorials Lab Practicals Fieldwork Placement Other TOTAL
Study Hours     2

    16

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
online time-controlled examination  1.5hrs    80       
CONTINUOUS Duration Timing
(Semester)
% of
final
mark
Resit/resubmission
opportunity
Penalty for late
submission
Notes
Assignment 2 Will be made available in week 6 of Semester 2, and the online submission date for this assignment is noon, Monday 26th April 2021 (Week 9).      10       
Assessment 1 Made available in Week 5 of the semester and the deadline for online submission of this assignment is noon, Monday 12th April 2021 (Week 7)      10