Classification and nomenclature of heterocyclic compounds. Aromatic heterocycles: five-atom and six-atom six--electron systems and benzo-fused ring systems. Criteria of aromaticity. Reactivity and tautomerism. Non-aromatic heterocycles. Ring synthesis: cyclization reactions and pericyclic reactions. Five- and six-membered ring systems with one or two heteroatoms and benzo-fused derivatives: synthesis, reactivity, and synthetic applications. Three-, four-, and seven-membered heterocycles.
T. L. Gilchrist: Heterocyclic Chemistry
Third Edition (or more recent)
Longman
Learning Objectives
The course is aimed to provide the students with a basic knowledge of heterocyclic chemistry and a general view of their numberless applications in synthetic, biological, and pharmaceutical domains.
Prerequisites
Courses required: none
Courses recommended: none
Teaching Methods
Total number of hours for Lectures (hours): 48
Type of Assessment
Oral final examination.
There are at least 8 examination sessions, especially in February, June, July, and September.
Course program
Classification and nomenclature of heterocyclic compounds. Aromatic heterocycles: five-atom and six-atom six--electron systems and benzo-fused ring systems. Criteria of aromaticity: bond lengths, ring currents, resonance energies. Reactivity and tautomerism. Non-aromatic heterocycles: bond angle strain, torsional energy barriers, conformational analysis. Ring synthesis: cyclization reactions (Baldwin’s classification) and pericyclic reactions (1,3-dipolar cycloadditions, Hetero Diels-Alder and [2+2] cycloadditions, cheletropic reactions, electrocyclic reactions). Six-membered ring systems with one heteroatom (pyridine, quinoline, isoquinoline): synthesis, reactivity, and synthetic applications. Five-membered ring systems with one heteroatom (pyrrole, indole, furan, thiophene): synthesis, reactivity, and synthetic applications. General features and applications of six- and five-membered ring systems with two or more heteroatoms. General features and applications of three-, four-, and seven-membered heterocycles.