Syllabus
Content of the subject:
1. Synthesis of heterocyclic systems - 3- and 4-membered heterocycles and their transformations. Selected syntheses of Tamiflu. Chemistry of oxaziridine, diazirene, dioxetane. Reactions leading to azetidine-2-one. Example of the use of epoxides in the synthesis of secondary insect metabolites.
2. Synthesis of heterocyclic systems - 5-membered saturated heterocycles. Less known reactions of tetrahydrofuran, thiolane and pyrrolidine. Chemistry of dioxolan, dihydrooxazole and, of course, azlactone.
3. Chemistry of heterocyclic systems - 5-membered heterocycles. Cycloadditions of furan, electrophilic aromatic substitutions on furan, pyrrole and thiofen, etc. Their deprotonation and transition metal catalysed couplings. Classical name reactions.
4. Chemistry of benzofuran, benzothiofen, benzoselenofen, indole and analogous condensed systems (annelated systems).
5. Chemistry of oxazole, benzoxazole, thiazole, imidazole and benzimidazole.
6. Synthesis of heterocyclic systems - 6-membered heterocycles containing nitrogen. Pyridine and its extremely rich chemistry (Zinke reaction, etc.). Preparation of quinoline and isoquinoline.
7. Chemistry of pyrimidine, quinazoline, preparation of BODIPA and porfin.
8. Chemistry of flavonoids.
Annotation
The course is focused on the chemistry of heterocyclic compounds. During the lesson, the relationships between structure, reactivity and stereochemistry will be discussed in detail.
Great emphasis will be placed on knowledge of organic chemistry, namely synthesis and tactics and strategies of functional groups protection.
While in small saturated heterocyclic circles, the exercise will discuss in detail the stereochemical aspects of opening these circles, in mid-size heterocycles, the emphasis will be placed on modern transformations of these systems (e.g. palladium-catalyzed transformations).
All the reactions discussed by the lecturer were used in his research and therefore, in addition to theory, the tips and tricks of practical organic chemistry will be discussed as well.
During the exercise, mechanisms of organic reactions such as fragmentation, nucleophilic aromatic substitutions, cycloadding, etc. will be repeated as well as physico-chemical properties of functional groups (e.g. pKa values).