Unit ORGANIC CHEMISTRY II

Course
Chemistry and technology of drugs
Study-unit Code
65005311
Location
PERUGIA
Curriculum
In all curricula
Teacher
Andrea Temperini
Teachers
  • Andrea Temperini
Hours
  • 132 ore - Andrea Temperini
CFU
11
Course Regulation
Coorte 2018
Offered
2020/21
Learning activities
Base
Area
Discipline chimiche
Academic discipline
CHIM/06
Type of study-unit
Obbligatorio (Required)
Type of learning activities
Attività formativa monodisciplinare
Language of instruction
Italian
Contents
Carbohydrates chemistry. Structure and nomenclature. Synthesis and reactivity of heterocyclics. Systematic (Hantzsch-Widman) nomenclature. Aromatic and nonaromatic heterocycles. Symthesis of pyrrole, pyridine, quinoline, indole. Cyclization reactions and Cycloaddition reactions in ring synthesis.Concepts of Organic synthesis. Conformation and Stereochemistry. Methods of ring formations: Diels-Alder reaction; Annelation methods; Ring Closure Reactions; Ring Cyclization. Preparation of small rings. Synthetically useful rearrangements. Organometallic chemistry. Alkylation of Enolates and other Carbon Nucleophiles. Hydration methods. Hydroxylation Methods. Reductions. Oxidation. Halogenation. Preparation of Alkenes. Stereoselective synthesis. Peptide synthesis. Some laboratory experiments to acquire the laboratory techniques and bibliography research.
Reference texts
Copies of slides on Unistudium Platform.Consultation texts:Advanced Organic Chemistry, 4th Ed., Part A and BFrancis A. Carey and Richard J. SundbergKluwer Academic / Plenum Publishers, New York March's Advanced Organic Chemistry, 6th Ed.Michael B. Smith and Jerry MarchJohn Wiley & Sons Inc., New York Organic Synthesis - Strategy and ControlP. Wyatt, S. WarrenJohn Wiley & Sons, Ltd, Chichester, England Basic Organic StereochemistryErnest L. Eliel, Samuel H. Wilen, Michael P. DoyleJohn Wiley & Sons Inc., New York Heterocyclic ChemistryT. L. GilchristLongman Scientific & Technical, Harlow (England) Strategic Applications of Named Reactions in Organic SynthesisL. Kurti, B. CzaboElsevier Academic Press Name Reactions (II Edition)A Collection of Detailed Reaction MechanismsJie Jack LiSpringer, Berlin
Educational objectives
The main aim of this teaching is to provide students with the bases needed to address the synthesis of a target molecule with moderate complexity. Main knowledge acquired will be:- understand the various possibilities for the functional group interchanges;-  incorporate in the synthetic strategy the newest methodologies for transition metal-catalyzed reactions and synthesys of carbocycles and heterocycles;- evaluate the use of chiral induction towards stereoselective synthesis of compounds;- analysis of a molecular structure and critical evaluation of the solution founded for its synthesis;The main competence will be:- provide a reasoned synthesis of a molecular target based on existing synthetic knowledge;- discuss on the advantages and disadvantages of the use of different reagents in standard organic synthesis;- identify the concepts and principles of organic synthesis and evaluate new metodological trends for the efficient synthesis of bioactive molecules;
Prerequisites
In order to be able to understand and apply the majority of the chemical reactions described within the Course, it is necessary to have successfully passed the Organic Chemistry I exam. Moreover, due to the new  topics introduced, knowledge of the principal organic reaction mechanisms represents a mandatory prerequisite for the student planning to follow this course with profit.
Teaching methods
The course is organized as follows:- lectures on all subjects of the course;- practical training at the organic synthesis laboratory. Students will be divided into couple and there will be seven tutorial concerning the basic techniques in the organic chemistry laboratory and some simple organic reactions.
Other information
Attendance is mandatory
Learning verification modality
The exam consists on an oral test that consists on an interview of about 60 minutes long aiming to ascertain the knowledge level and the understanding capability acquired by the student on theoretical and methodological contents as indicated on the program. The oral exam will also test the student communication skills and his autonomy in the organization and exposure of the theoretical topics. Moreover, there is no exam for practical training at the organic synthesis laboratory but only e brief test concerning the practical skills acquired during the laboratory activity
Extended program
Carbohydrates. Structure and nomenclature. Chemistry of carbohydrates. Functional groups protection and deprotection. Synthesis of Strychnine. Heterocyclic chemistry. Systematic Nomenclature. (Hantzsch-Widman). Aromatic and nonaromatic heterocycles. Symthesis of pyrrole, pyridine, quinoline, indole. Cyclization reactions and Cycloaddition reactions in ring synthesis. Concepts of Organic synthesis. Conformation and Stereochemistry. Methods of ring formations: Diels-Alder reaction; Annelation methods; Ring Closure Reactions; Cyclization.Preparation of small rings. Synthetically useful rearrangements. Organometallic chemistry of Li, Mg, Cu, Zn, Pd and Ni. Homo and heterocoupling. Alkylation of Enolates and Other Carbon Nucleophiles. Hydration methods. Hydroxylation Methods. Reductions. Oxidation. Halogenation. Preparation of Alkenes. Stereoselective synthesis. Peptide synthesis. For the laboratory it will be carried out various experiments to acquire the manual base and the various laboratory techniques and bibliography research.
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