OVERVIEW

More than half of the known organic compounds contain a cyclic system, typically heterocyclic.
Heterocyclic systems abound among natural compounds, and many of them are of great importance in biological processes.
They therefore play an enormous role especially in the pharmacological field, and more generally in many application fields including that of innovative materials.

AIMS AND CONTENT

LEARNING OUTCOMES

Provide an adequate knowledge of the chemistry (synthesis, structure, reactivity) of heterocyclic systems, of high importance both in the biological/pharmacological and industrial/technological fields. Taking inspiration from the behavior of some representative heterocycles, some insights into the involved reaction mechanisms will also be provided.

AIMS AND LEARNING OUTCOMES

The course aims to provide students with an adequate knowledge of the structure, properties, synthesis and reactivity of the main classes of heterocyclic systems, starting from some representative heterocycles. The nomenclature of these systems will be detailed, also through appropriate exercises.

PREREQUISITES

For an optimal fruition of the teaching, the knowledge of the main concepts of General Chemistry and Organic Chemistry 1, 2 and 3 is needed.

TEACHING METHODS

6 ECTS of lectures (including exercises).

SYLLABUS/CONTENT

Heterocyclic compounds
Definition, importance, classifications, nomenclature.

Aromatic heterocycles
Heteroaromaticity, electron-rich and electron-poor systems, description of the π electronic distribution and quantification of aromaticity, basicity and acidity of nitrogenous heterocycles, tautomeric equilibria.

Reactivity of aromatic heterocycles
Electrophilic and nucleophilic substitution reactions, metalation and ring opening.

Synthesis of aromatic heterocycles
Synthesis of the main heteroaromatic scaffolds, pericyclic ring-synthesis processes (cycloadditions, electrocyclizations, sigmatropic rearrangements) and ionic processes (nucleophilic and electrophilic substitutions, nucleophilic additions, condensations).

RECOMMENDED READING/BIBLIOGRAPHY

​• T. EICHER, S. HAUPTMANN, A. SPEICHER The Chemistry of Heterocycles
• K. MILLS, J. A. JOULE Heterocyclic Chemistry, Wiley
• L. D. QUIN, J. A. TYRELL Fudamentals of Heterocyclic Chemistry, Wiley

TEACHERS AND EXAM BOARD

LESSONS

LESSONS START

See here 

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

EXAM DESCRIPTION

The student will have to take an oral exam, in front of a commission of at least two people, using an appropriate writing support (blackboard or other) on which to develop the topics of the interview, especially with regard to the nomenclature exercise.

The student can freely choose to start the exam with a digital presentation on an in-depth discussion of a topic of the program through the analysis of a literature article, to be agreed with the teacher.

For students with disabilities or with DSA, please refer to the Other Information section.

ASSESSMENT METHODS

The exam consists of an oral test lasting about one hour in which the student's knowledge of the properties, reactivity and synthesis of the most important heterocycles  will be verified, as well as their nomenclature (applied to a practical example); among the exam topics, it may be required to comment an article from recent literature.

FURTHER INFORMATION

Students who have valid certification of physical or learning disabilities on file with the University and who wish to discuss possible accommodations or other circumstances regarding lectures, coursework and exams, should speak both with the instructor and with Professor Sergio Di Domizio (sergio.didomizio@unige.it), the Department’s disability liaison.