COURSE OBJECTIVE: To introduce students to the main classes of heterocyclic compounds and highlight their importance in research, organic reactions, and industrial applications.
COURSE SYLLABUS
1. Introduction to heterocyclic compounds: structure and characteristics of heterocycles; classification; aromaticity; examples of pharmacologically active heterocyclic compounds.
2. Nomenclature of monocyclic compounds: Hantzsch?Widman system.
Nomenclature of bicyclic compounds, macrocyclic polyethers, and annulenes
Laboratory ? Entry colloquium
3. Three-membered heterocycles: oxirane, thiirane, aziridine: structure, properties, reactivity, reactions, and synthesis
Laboratory ? Synthesis of the pyrimidine ring
4. Four-membered heterocycles: structure, properties; oxetane, thietane, azetidine, oxete, thiete, azete: reactions and synthesis
Laboratory ? Synthesis of the pyrimidine ring
5. Four-membered heterocycles: structure, properties; oxetane, thietane, azetidine, oxete, thiete, azete: reactions and synthesis
Laboratory ? Isolation of the pyrimidine ring by column chromatography
6. Five-membered heterocycles of the alkane and alkene series containing oxygen, sulfur, and nitrogen: structure, properties, reactions, and synthesis
Laboratory ? Isolation of the pyrimidine ring by column chromatography
7. 1st partial test
8. Furan, thiophene, and pyrrole: properties; reactivity; reactions at the C-atom and at the heteroatom, metalation reactions, electrocyclic reactions; benzo[b]furan, benzo[b]thiophene, and indole: the most important reactions and synthesis.
Laboratory ? Synthesis of the bicyclic furopyrimidine ring
9. Azoles and benzoazoles: properties; reactivity, reactions with electrophilic reagents at the C- or N-atom, reactions with nucleophilic reagents, metalation reactions, electrocyclic reactions; oxazoles, thiazoles: the most important reactions and synthesis.
Laboratory ? Synthesis of the bicyclic furopyrimidine ring
10. Six-membered heterocycles: properties; pyridine, pyridinones, aminopyridines, alkylpyridines, pyridine N-oxides: reactions and synthesis.
Laboratory ? Synthesis of the bicyclic furopyrimidine ring
11. Six-membered heterocycles: properties; pyridine, pyridinones, aminopyridines, alkylpyridines, pyridine N-oxides: reactions and synthesis.
Laboratory ? Isolation of the bicyclic furopyrimidine ring by column chromatography
12. Benzopyridines: properties, reactivity; synthesis; quinoline and quinoline derivatives: reactions with electrophilic and nucleophilic reagents, metalation reactions, reactions with reducing agents.
Laboratory ? Isolation of the bicyclic furopyrimidine ring by column chromatography
13. Pyran, pyrylium salts, and pyranones: structure, properties, reactivity, reactions with electrophilic and nucleophilic reagents; synthesis; coumarins, chromones, and flavonoids.
Laboratory ? Isolation of the bicyclic furopyrimidine ring by column chromatography
14. Seven-membered heterocycles with oxygen and nitrogen: structure, properties, reactions, synthesis.
Macrocyclic heterocycles: structure, properties, and synthesis; crown ethers, cryptands, metallacrowns, spherands.
Laboratory ? Final colloquium
15 2nd partial test
Prerequisites for course enrollment: Passed courses: all courses of the 1st year of study, Organic Chemistry I, Organic Chemistry II;
Prerequisites for taking the course exam:
Completed laboratory exercises;
Development of students' general and specific competencies:
General competencies:
Apply the principles of modern synthetic organic chemistry and literature or own experimental data in solving chemical engineering problems.
Specific competencies:
Apply synthesis reactions and reactions involving heterocyclic compounds and their derivatives in synthetic organic and medicinal chemistry.
Student obligations in teaching and methods of fulfilling them:
Students are required to attend lectures
Students are required to complete all laboratory exercises
Students are required to take the knowledge assessments
Method of course delivery:
Lectures (ex cathedra)
E-learning lectures
Laboratory exercises (practical work in groups under the supervision of an assistant)
Consultations by arrangement with students
Method of knowledge assessment and examination:
2 partial tests during the semester (60% of points on each test exempts the student from the oral exam)
Written exam (50% of points required to pass)
Oral exam
Method of monitoring the quality and success of the course:
Student survey
Course learning outcomes:
Recognize and name individual heterocyclic compounds
Explain the influence of heteroatoms in ring structures
Discuss aromaticity in heteroaromatic compounds
Plan a synthetic route to a specific heterocyclic system
Explain the factors affecting the reactivity of functional groups in ring structures
Carry out experiments in the laboratory
Program-level learning outcomes to which the course contributes:
Solve qualitative and quantitative problems by applying appropriate chemical principles and theories
Interpret chemical information and data
Search for information available on the Internet
Apply standard laboratory procedures and instrumentation for preparative or analytical purposes, for organic and inorganic systems
Apply techniques and methods for measuring chemical quantities, properties, or changes
Interpret the results of laboratory observations and measurements, their significance, and their connection to the corresponding theory
Use information technology
Plan time management
Organize independent work
Required literature:
T. Gazivoda Kraljević, M. Hranjec, Osnove kemije heterocikličkih spojeva, FKIT/HDKI, Zagreb, 2020.
J. A. Joule, K. Mills, Heterocyclic Chemistry, Wiley-VCH, 5th Ed, 2010.
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