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
•Knowledge and comprehension.
•Ability to apply knowledge and comprehension.
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 to be used as requirements (required and/or recommended)
Required courses: none
Recommended courses: none
Teaching Methods
Frontal lectures: 48 hours
Type of Assessment
Oral final examination.
Assessment of the comprehension of the treated subjects, ability of critical reasoning, quality of the presentation.
There are at least 8 examination sessions, especially in February, June, July, and September.
Registration on line is necessary to take the examination. The sessions for the academic year 2016/2017 are available at the link: https://sol.unifi.it/docprenot/docprenot
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.