Heterocyclic Compounds and Application of Organometallic Chemistry in Synthesis
A.Y. 2024/2025
Learning objectives
The aim of the course is to improve how a synthesis of heterocycle compounds should be realized by using classic organic methodology or by heterogeneous and/or homogeneous metal-assisted catalysis.
Expected learning outcomes
The expected learning outcomes will be focalized on improvement of the knowledge in the field of organic chemistry, in particular on capability of the student to understand the reactivity and to propose synthetic ways for the construction of simple heterocyclic molecules. The student should be able to propose alternative synthetic methodology based on organometallic chemistry useful in academic research laboratories and in industrial reality.
Lesson period: Second semester
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Single course
This course can be attended as a single course.
Course syllabus and organization
Single session
Lesson period
Second semester
Prerequisites for admission
Basic knowledge of Organic and Organometallic Chemistry
Assessment methods and Criteria
Written exam on practice exercises on synthesis and reactivity of heterocycle compounds.
Oral presentation about a topic in organometallic chemistry chosen by the student.
Oral presentation about a topic in organometallic chemistry chosen by the student.
Heterocyclic compounds
Course syllabus
Heterocyclic compounds: naming and strategies of synthesis.
Heterocycles with three or four atoms containing nitrogen, oxygen and sulphur: synthesis, reactivity
and opening reactions.
Heteroaromatic compounds: heteroaromaticity, electron-poor and electron-rich systems; molecular
orbitals of heterocyclic compounds.
Reactivity of heterocycles with electrophyles, charge-control and frontier-control. Dipolar
cycloaddition reactions.
Furane, thiophene, pyrrole, isoxazole, imidazole and benzo-derivatives: synthesis, methods of
functionalization and metallation reactions. Reactions of reduction, oxidation, electrophylic
substitution. Biologically active derivatives.
Pyridine, quinoline, isoquinoline, 1,2-, 1,3- 1,4-diazines, purines: synthesis, reaction with
electrophyles and nucleophyles. N-oxidation and reactivity of N-oxides. Reactivity of various
functional groups. Biologically active pyridines.
Heterocycles as synthons in organic synthesis.
Heterocycles with three or four atoms containing nitrogen, oxygen and sulphur: synthesis, reactivity
and opening reactions.
Heteroaromatic compounds: heteroaromaticity, electron-poor and electron-rich systems; molecular
orbitals of heterocyclic compounds.
Reactivity of heterocycles with electrophyles, charge-control and frontier-control. Dipolar
cycloaddition reactions.
Furane, thiophene, pyrrole, isoxazole, imidazole and benzo-derivatives: synthesis, methods of
functionalization and metallation reactions. Reactions of reduction, oxidation, electrophylic
substitution. Biologically active derivatives.
Pyridine, quinoline, isoquinoline, 1,2-, 1,3- 1,4-diazines, purines: synthesis, reaction with
electrophyles and nucleophyles. N-oxidation and reactivity of N-oxides. Reactivity of various
functional groups. Biologically active pyridines.
Heterocycles as synthons in organic synthesis.
Teaching methods
Lectures supported by practical activities about the topics developed during the lessons.
Application of organometallic chemistry in synthesis
Course syllabus
Introduction to metalorganic chemistry: metals, trans effect, soft and hard ligands, retro donation.
Electro neutrality, types of ligands, 18 electrons rule.
Limitations of 18 electrons rule, number of electrons in a reaction, oxidation state, coordination
number and geometry, complexation effect.
Differences between metals, outer-sphere coordination, mono and di-phosphines, mixed ligands,
catalytic cycles and reactions.
Reduction reactions: asymmetric hydrogenation of olefins and carbonylic groups.
Reduction reactions: asymmetric hydrogen transfer of ketones and imines.
Advantages of asymmetric catalysis.
Hydrofomilation.
Hydrocarbonylation.
Hydroesterification.
Heck reaction.
Hydrocyanation.
Allylic alkylation.
From laboratory to plant of pharmaceutical industry.
Electro neutrality, types of ligands, 18 electrons rule.
Limitations of 18 electrons rule, number of electrons in a reaction, oxidation state, coordination
number and geometry, complexation effect.
Differences between metals, outer-sphere coordination, mono and di-phosphines, mixed ligands,
catalytic cycles and reactions.
Reduction reactions: asymmetric hydrogenation of olefins and carbonylic groups.
Reduction reactions: asymmetric hydrogen transfer of ketones and imines.
Advantages of asymmetric catalysis.
Hydrofomilation.
Hydrocarbonylation.
Hydroesterification.
Heck reaction.
Hydrocyanation.
Allylic alkylation.
From laboratory to plant of pharmaceutical industry.
Teaching methods
Lectures supported by practical activities about the topics developed during the lessons.
Application of organometallic chemistry in synthesis
CHIM/03 - GENERAL AND INORGANIC CHEMISTRY - University credits: 4
Lessons: 32 hours
Heterocyclic compounds
CHIM/06 - ORGANIC CHEMISTRY - University credits: 4
Lessons: 32 hours