Chemistry
Name: Advanced Heterocyclic Chemistry
Catalog Number: 412028Y Hours/Credits: 40/2
Prerequisite(s):
Organic Synthesis, Physical Chemistry
Course Description:
This course is the basic course for chemistry graduates, especially for the students in the majors of Organic Synthesis and Medicinal Chemistry, also as a required or elective course for others such as the students focusing on the organic functional materials synthesis, organometallic catalysis, biochemistry, and chemical biology. Students are required to have a solid fundamentals of synthetic organic chemistry, able to study the structural properties, synthetic methods of heterocyclic compounds and their reactions and mechanism, by using the theory, concepts and methods of organic chemistry and physical organic chemistry. Systematic understanding the practical application of heterocyclic compounds in the pharmaceutical, pesticides, materials, analysis, catalytic, combining with the recent literature, the students can think about the opportunities and challenges in the study of heterocyclic chemistry
Course Content:
This course focuses on the synthesis, reaction mechanism and application of heterocyclic compounds. Heterocyclic compounds are distributed broadly in nature, and their number accounted mostly proportion for the known organic compounds (more than 30 million). Many important substances such as chlorophyll, hemoglobin, nucleic acids, as well as natural drugs and synthetic drugs in clinical applications having a significant effect, contain the structure of heterocyclic compounds. Alkaloids are the active ingredients of Chinese herbal medicine, majority of them are nitrogen-containing heterocyclic compounds. Heterocyclic chemistry and medicine, pesticide, and the life sciences, materials science is deep closely related. Having the cyclic structures, one or more carbon atoms in ring of Heterocyclic compounds are replaced by the non-carbon atoms( called as heteroatoms) such as O, S, N, P, of Se, As, Sb, and Bi, Si. This course, firstly, will focus on to discuss the properties, synthesis, reactions and applications of the saturated small ring heterocycles( in 3,4-membered ring) , and then focuses on the similar discussion on the unsaturated heterocyclic compounds which are relatively stable and have different aromatic characters in 5,6,7,8 or larger membered ring. Chapter 1 Classification and naming of heterocyclic compounds Heterocyclic compounds can be divided saturated heterocyclic and unsaturated heterocyclic based on the valences of the chemical bonds, aromatic unsaturated heterocyclic compounds will be focused on. In the way of heterocyclic skeleton, there are single-ring heterocycles and fused heterocycles. Single-ring heterocycles are in the 3,4,5,6,7,8 or more/large membered ring, or fused heterocyclic compounds are in the way of benzene fused heterocyclic and or non-benzene fused heterocycles according to the form of fused ring. Chapter 2 Electronic structure and physical properties of general heterocyclic compounds The structures of 5-membered ring heterocyclic compounds pyrrole, furan, thiophene are similar to that of benzene, the electronic structures of imidazole, pyrazole, thiazole are similar to the above rings. 6-membered heterocyclic ring structure can be illustrated by using pyridine as an example. Chapter 3 Heterocyclic compounds in smaller ring with strain force and large ring 3.1 Three-membered heterocyclic compounds 3.2 Four-membered heterocyclic compounds 3.3 Heterocyclic compounds in seven-, eight-membered or a large ring Chapter 4 The properties, synthesis, reactions and mechanisms of some important heterocyclic compounds and their derivatives Including reactions with electrophiles, nucleophiles, oxidants, free radical reagents, reducing agents, alkali reaction, photochemical reaction and electrocyclization 4.1 Five-membered ring heterocyclic compounds and their derivatives: Furan, Thiophene, Pyrrole, Indole & Derivatives 4.2 Six-membered ring heterocyclic and derivatives: pyridine, quinoline, pyrimidine, purine and derivatives 4.3 Azoles and multi-heteroatom compounds, triazine Azole and Azine, 4.4 Heterocyclic ketene aminals and their drug effects: synthon in the synthesis of a new class of heterocyclic compounds 4.5 TTF and its derivatives and their optical features 4.6 The Crown Ether 4.7 Pyran and derivatives 4.8 Heterocyclic compounds containing B, P, Si elements or metals (Se, As, Sb, Bi) Chapter 5 The application of heterocyclic compounds 5.1 Heterocyclic and catalysis: metal complex catalysis, heterocyclic small molecule catalysts, etc. 5.2 Application in materials: dyes, conductive polymers, organic photovoltaic materials 5.3 Heterocyclic and spices, drugs (alkaloids, etc.), pesticides, food, cosmetics, etc. 5.4 Heterocycles and molecular recognition, molecular devices and self-assembly. 5.5 Heterocyclic ionic liquid and its application (definition, structure type, and scope of application)
TextBooks:
1) Edited by J A Joule, K.Mills, translated by Ye-Cheng YOU, Da-Bin GAO, Heterocyclic Chemistry, Science Press, Beijing, 2004, ISBN: 7-03-012736-6, http://www.sciencep.com. 2) Edited by Theophil Eicher and Siegfried Hauptmann, translated by Run-Tao LI et.al., Heterocyclic Chemistry - structure, reactions, synthesis and applications, Chemical Industry Press, 2006, Beijing, (ISBN: 7 - 5025-7960-5).
Reference:
1) YAN-Lai Zhao, Sen-Qaun He, Cheng-De Xu edited, Introduction to Heterocyclic Chemistry, Higher Education Press, Beijing, 1992, 1st edition, ISBN :7-04-002 236-2 / O.771. http://eng.hep.com.cn