HETEROCYCLIC CHEMISTRY
Academic year and teacher
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- Versione italiana
- Academic year
- 2015/2016
- Teacher
- CLAUDIO TRAPELLA
- Credits
- 6
- Didactic period
- Primo Semestre
- SSD
- CHIM/06
Training objectives
- The course deals with the properties and synthesis of heterocyclic compouns with a particular enphasis to the organometallic chemistry associated to the synthesis of heterocyclic molecules. The course will be divided in two fundamental parts, the first one of about 14 hours and the second one of about 22 hours of frontal lessons. During the first part of the course the students will be introduced to the synthesis of 5 and 6 member heterocyclic rings and the fundamental rule for the formation of heterocycle. During the second part of the course we will take into accont the most important organometallic reactions for the formation of heterocyclic rings.
The knowledge that will be acquired are the reactivity forecast of a heterocyclic compound in organic synthesis , the procedures and rules for the synthesis of 5 and 6 member ring heterocyclic compounds. The skills that the student must acquire are the ability to organize a multi-stage synthesis for the preparation of heterocyclic compounds and their use in the synthesis of pharmaceutical and industrial interest products. Prerequisites
- Organic Chemistry, advanced Organic chemistry general chemistry
Course programme
- Properties and synthesis of five and six member heterocyclic ring, the anomeric effect. Pyridine as example for understanding the different reactivity between aromatic heterocycle and benzene. (6h) The Thorpe rule, the Baldwin rule, cycloaddiction in particular copper catalyzed (Huisgen).(6h) Making heterocycle by nucleophylic substitution, Suzuki, Neghisi and Sonogashira reaction for making heterocyclic ring. (8h) The Heck reaction and the apto number of palladium complex.
IUPAC nomenclature of fused heterocyclic ring. (8h) The catalytical cycle of palladium chemistry, differences between different reaction conditions. The importance of palladium ligands for the formation of new carbon-carbon bond. (8h) Didactic methods
- 36 lectures in classroom
Learning assessment procedures
- Oral examination: the examination consists in 3 questions on the program subdivided as it follows:
First question about the reactivity of aromatic heterocycle.
Second question about one of the catalytical cycle of Sonogashira, Suzuki, Heck or Huisgen reactions
Third question about the rule for the formation of heterocycle.
During the examination the student have to demonstrate a proper chemical languages and the knowledge of the heterocyucle chemistry associated to the organometallic chemistry. Reference texts
- J.A. Joule and K. Mills, Heterocyclic Chemistry, fifth edition Wiley.
J.J.Li, G.W. Gribble; Palladium in heterocyclic chemistry. Pergamon press
