Chemistry of Heterocyclic Compounds 1200-2SPEC122M
This lecture covers the following topics:
- Three-membered rings with oxygen, nitrogen and sulphur; biological activity (pheromones, anti-cancer drugs), synthesis and reactivity;
- Four-membered rings; synthesis and reactivity; beta-lactam antibiotics
- Fife-membered rings (furans, pyroles, thiophenes); synthesis; utilization in drug synthesis;
- Six-membered rings (pyridines, pyranes); synthesis and reactivity (electrophilic and nucleophilic substitution); utilization in alkaloid synthesis;
- Quinolines, isoquinolines, indoles; occurrence in the nature; utilization in synthesis of dyestuffs and drugs;
- Application of heterocyclic compounds in organic synthesis;
- Heterocyclic compounds in new technologies;
Course coordinators
Type of course
Mode
General: Classroom | Term 2024L: Blended learning | Term 2025L: Classroom |
Requirements
Prerequisites (description)
Learning outcomes
Knowledge
After completing the course, the student:
• knows the nomenclature systems for heterocyclic compounds;
• knows the basic classes of heterocyclic compounds and the principles of their classification according to ring structure, number, and type of heteroatoms;
• knows selected methods for the synthesis of the discussed heterocyclic compounds;
• knows the characteristic reactions of heterocyclic compounds and understands the factors influencing their reactivity (ring structure, type of heteroatom);
• understands the importance of heterocyclic systems as significant structural elements of natural compounds and derivatives exhibiting biological activity.
Skills
After completing the course, the student:
• is able to recognize and classify heterocyclic compounds based on their structure;
• is able to design a synthetic pathway for selected heterocyclic compounds;
• is able to predict reactions of heterocyclic compounds based on their structure and electronic properties;
• is able to explain the influence of the heteroatom and ring structure on the reactivity of a given heterocyclic system;
• is able to identify natural compounds containing a heterocyclic ring in their structure;
• is able to relate the structure of selected heterocyclic systems to their chemical properties and potential applications.
After completing the course, the student will know the fundamentals of synthesis, reactivity, and biological activity of the discussed heterocyclic compounds.
In particular:
KNOWLEDGE
K_W01, K_W05, K_W06, K_W08, K_W10
After passing the course, the student:
• has extended knowledge of the place of chemistry within the system of exact and natural sciences, and of its significance for the development of humanity;
• possesses advanced knowledge and skills in a selected chemical specialization, enabling the use of methods and concepts appropriate for that specialization and allowing independent research work;
• has knowledge of mathematics necessary for the quantitative description of chemical phenomena and processes relevant to a given chemical specialization;
• possesses advanced knowledge and skills in computational methods appropriate for a given chemical specialization;
• has a good understanding of current trends in the development of chemistry and the latest scientific discoveries in a given chemical specialization.
SKILLS
K_U03, K_U08, K_U11
After passing the course, the student:
• is able to apply appropriate research methods, techniques, and tools within a given chemical specialization necessary to explain a posed problem;
• possesses advanced knowledge and skills enabling the use of professional literature, databases, and other information sources, as well as the ability to evaluate the reliability of acquired information;
•is able to discuss the place of chemistry within the system of exact and natural sciences and its significance for the development of our civilization.
Assessment criteria
Assessment Rules:
➢ Attendance at lectures is mandatory.
➢ Written in-class examination.
➢ Two partial tests (optional) – possibility of passing the course based on their results.
➢ Preparation of a 5–7 minute presentation based on a scientific publication from the last decade concerning heterocyclic compounds; this may:
✓ improve the final grade by half a grade;
✓ result in a passing grade, provided that the average score from the tests/exam exceeded 30%.
Practical placement
none
Bibliography
1. Heterocyclic Chemistry, John A. Joule, Keith Mills, A John Wiley & Sons, Ltd.,
Publication;
2. I. Młochowski, Chemia związków heterocyklicznych, PWN
3. T. Eichler, S. Hauptmann, Wiley-VCH, Weinheim, The Chemistry of
Heterocycles;
4. Julio Alvarez-Builla, Juan Jose Vaquero, and José Barluenga, Modern
Heterocyclic Chemistry Volume 4;
5. John A. Joule, Keith Mills, Heterocyclic Chemistry at a Glance, Blackwell
Publishing;
6. Stephen Po Stanforth, Natural Product Chemistry at a Glance, Blackwell
Publishing;
Notes
|
Term 2024L:
None |
Term 2025L:
None |