1
课程详述
COURSE SPECIFICATION
以下课程信息可能根据实际授课需要或在课程检讨之后产生变动。如对课程有任何疑问，请联
系授课教师。
The course information as follows may be subject to change, either during the session because of unforeseen
circumstances, or following review of the course at the end of the session. Queries about the course should be
directed to the course instructor.
1.
课程名称 Course Title
杂环化学 Heterocyclic Chemistry
2.
授课院系
Originating Department
化学系 Department of Chemistry
3.
课程编号
Course Code
CH325
4.
课程学分 Credit Value
3
5.
课程类别
Course Type
专业选修课 Major Elective Courses
6.
授课学期
Semester
秋季 Fall
7.
授课语言
Teaching Language
中英双语 English & Chinese
8.
授课教师、所属学系、联系方
式（如属团队授课，请列明其
他授课教师）
Instructor(s), Affiliation&
Contact
（For team teaching, please list
all instructors）
段乐乐副教授，化学系
Dr. Lele Duan, Associate Professor, duanll@sustech.edu.cn, Dept. of Chem.
9.
实验员/助教、所属学系、联系
方式
Tutor/TA(s), Contact
无 NA
10.
选课人数限额(可不填)
Maximum Enrolment
（Optional）
授课方式
Delivery Method
讲授
Lectures
习题/辅导/讨论
Tutorials
实验/实习
Lab/Practical
其它(请具体注明)
Other（Please specify）
总学时
Total
11.
学时数
Credit Hours
48
0
0
0
48
2
12.
先修课程、其它学习要求
Pre-requisites or Other
Academic Requirements
化学原理 A（CH101A）
13.
后续课程、其它学习规划
Courses for which this course
is a pre-requisite
14.
其它要求修读本课程的学系
Cross-listing Dept.
教学大纲及教学日历 SYLLABUS
15.
教学目标 Course Objectives
设计该课程的目的是为了让学生了解杂环化合物的一般性质以及杂环化学的基础理论知识，并在此基础之上让学生了解杂
环化合物的反应活性以及反应机理，为其在今后的学习工作中解决杂化化学问题提供理论基础。该课程内容涉及到杂环化
合物的系统介绍、命名、结构和反应机理。该课程将开阔学生对杂环化学的认识，结合日常生活中接触到的杂化化合物，
普及杂环化合物在生命科学中的应用。
Heterocyclic Chemistry is designed to give a general but fundamental theoretical understanding of the chemistry of
compounds that contain heteroatoms in the ring, their syntheses, reactions and uses as catalyst. Heterocyclic Chemistry
also aims to encourage more undergraduate students who interested in heterocyclic chemistry to carry out related
research at their seniors.
The topics of Heterocyclic Chemistry include: introduction to heterocyclic chemistry, nomenclature of heterocyclic
compounds, structure of heterocyclic compounds, common reaction types in heterocyclic chemistry, various kinds of
heterocyclic compounds, and heterocyclic chemistry in life and so on.
As its wide application on life science, materials science and medicine engineering, heterocyclic chemistry is one of the
most cutting-edge field in organic chemistry. A special point for this course broad student’s horizon on heterocyclic
systems by giving an introduction to heterocyclic chemistry. In addition, the ability of analysing and solving problems
should be improved during this course.
16.
预达学习成果 Learning Outcomes
完成课程之后，学生预期能够：
够熟练对简单杂环化合物进行命名；
对杂环化学有更深刻的认识，了解不同杂环体系的反应性质；
了解杂环化学在医药中的重要应用。
Upon successful completion of this course, the student will be able to:
Compare the chemistry of the heterocycles with that of benzene;
Tell the uses of various heterocycles;
Assess the role of heterocycles in health care.
17.
课程内容及教学日历 （如授课语言以英文为主，则课程内容介绍可以用英文；如团队教学或模块教学，教学日历须注明
主讲人）
Course Contents (in Parts/Chapters/Sections/Weeks. Please notify name of instructor for course section(s), if
this is a team teaching or module course.)
3
Section 1: Introduction to Heterocyclic Chemistry 杂环化学导论（1 课时）
A selection of the structures, names and standard numbering of the more common heteroaromatic systems and some
common non-aromatic heterocycles, are shown in this chapter.
本节主要介绍一些常见的杂芳体系和非芳香杂环的结构和名称。
Section 2: Heterocyclic Nomenclature 杂环化合物的命名（1 课时）
Structures of benzene, naphthalene, pyridines, pyridiniums, quinolines, isoquinolines, diazines (illustrated using
pyrimidine), pyrroles, thiophenes and furans, indoles and azoles (illustrated using imidazole).
本节主要对结构中含有苯、萘、啶类化合物、吡啶、喹啉、异喹啉、吡咯、噻吩和呋喃、吲哚的化合物进行命名。
Section 3: Structure of Heteroaromatic Compounds 杂环化合物的结构（3 课时）
There are some ideas and reagents and reaction methodologies and reactivity patterns that turn up again and again in
heterocyclic chemistry and we summarise and explain these in detail in this chapter.
本节主通过详细地总结，并解释在杂环化学中有一些试剂会反复发生的反应方法和反应模式。
Section 4: Common Reaction Types in Heterocyclic Chemistry 杂环化学中常见的反应类型（3 课时）
We have gathered a range of examples of typical palladium-catalysed reactions of all heterocyclic systems together in
this chapter as they can be applied generally across the whole range, with the nature of the heterocycle only being
reflected in secondary effects such as rates and selectivity.
在本节中，我们收集了一系列典型的所有杂环体系钯催化反应的例子，因为它们可以广泛应用于整个范围，杂环的性质只
反映在速率和选择性等副作用中。
Section 5: Palladium in Heterocyclic Chemistry 杂环化学中的钯（4 课时）
Electrophilic addition to nitrogen, Electrophilic substitution at carbon, Nucleophilic substitution, Substitution of hydrogen,
Substitution of leaving groups, Nucleophilic addition to pyridinium salts, C-metallated pyridines, Palladium(0)-catalysed
reactions, Oxidation and reduction, Pericyclic reactions, Alkyl and carboxylic acid substituents, Oxygen substituents, N-
Oxides, Amine substituents, Ring synthesis -disconnections.
本节主要讲述杂环化学中钯，分别从氮的亲电加成、碳亲电取代、亲核取代、氢取代、离去基团的取代、吡啶盐的亲核加
成、C 金属吡啶、钯催化反应、氧化还原、烷基和羧酸取代基、氧取代基，N-氧化物、胺取代基、环合成-断开进行介绍。
Section 6: Diazines 二嗪类化合物（4 课时）
The diazines – pyridazine, pyrimidine and pyrazine – show many similarities to pyridines with respect to their reactivities,
but to an exaggerated degree. In particular, the presence of two nitrogens, both as imines, results in increased electron
deficiency at carbon and hence an increased susceptibility to nucleophilic addition but an increased resistance to
electrophilic attack.
本节主要讲述二嗪类化合物，其中二嗪类哒嗪、嘧啶和吡嗪与吡啶在反应性方面有许多相似之处，特别是两个氮素的存在
作为亚胺，导致电子缺陷在碳中增加，因此对亲核加成的敏感性增加，但对亲电攻击的抗性增加。
Section 7: Quinolines and Isoquinolines 喹啉类和异喹啉类（3 课时）
Electrophilic addition to nitrogen, Electrophilic substitution at carbon, Nucleophilic substitution, Substitution of leaving
groups, Nucleophilic addition to quinolinium/isoquinolinium salts, C-Metallated quinolines and isoquinolines,
4
Palladium(0)-catalysed reactions, Oxidation and reduction, Alkyl substituents, Oxygen substituents, N-Oxides.
本节主要讲述喹啉类和异喹啉，分别从氮的亲电加成、碳亲电取代、亲核取代、离去基团的取代、喹啉/异喹啉盐的亲核加
成、C-金属喹啉和异喹啉、钯催化的反应、氧化和还原、氧取代进行介绍。
Section 8: Pyryliums, Benzopyryliums, Pyrones and Benzopyrones 吡喃酮和苯并吡喃酮（2 课时）
Pyrylium salts, Nucleophilic addition, Ring-opening reactions of 2H-pyrans, Oxygen substituents – pyrones and
benzopyrones, Ring synthesis of pyryliums from 1,5-diketones (1,2-bond made), Ring synthesis of 2-pyrones from 1,3-
keto-aldehydes, Ring synthesis of 1-benzopyryliums, coumarins and chromones.
本节主要讲述吡喃酮和苯并吡喃酮，分别从吡喃盐、亲核加成、吡咯的开环反应、氧取代基-吡喃酮和苯并吡喃酮、1,5-二
酮（1,2-键）合成吡喃酮等方面进行介绍。
Section 9: Pyrroles 吡咯类化合物（2 课时）
Electrophilic substitution at carbon,N-Deprotonation and N-metallated pyrroles, C-Metallated pyrroles, Palladium(0)-
catalysed reactions, Oxidation and reduction.
本节主要讲述吡咯类化合物，分别从去质子化和金属吡咯、C 金属吡咯、钯催化反应、氧化和还原的亲电取代等方面进行
介绍。
Section 10: Indoles 吲哚类化合物（4 课时）
Electrophilic substitution at carbon, N-Deprotonation and N-metallated indoles, C-Metallated indoles, Palladium(0)-
catalysed reactions, Oxidation and reduction, Pericyclic reactions, Reactivity of side-chain substituents, Oxygen
substituents, Ring synthesis- disconnections, Synthesis of indoles from arylhydrazones, Synthesis of indoles from ortho-
nitrotoluenes, Synthesis of indoles from ortho-aminoaryl alkynes, Synthesis of indoles from ortho-alkylaryl isocyanides,
Synthesis of indoles from ortho-acyl anilides, Synthesis of isatins from anilines, Synthesis of oxindoles from anilines,
Synthesis of indoxyls from anthranilic acids.
本节主要讲述吲哚类化合物，分别从 N-去质子化和 N-金属化吲哚的亲电取代、C 金属化吲哚、钯催化反应、氧化和还
原、周环反应、侧链取代基的反应性、氧取代基、环合成-脱开、吲哚的合成芳基腙，邻硝基甲苯类吲哚类化合物的合成，
邻氨基芳基炔烃吲哚的合成，邻位烷基芳基异氰酸酯合成吲哚类，邻酰基苯胺类吲哚的合成，苯胺类化合物的合成，苯胺
类吲哚类化合物的合成进行介绍。
Section 11: Furans and Thiophenes 呋喃和噻吩类化合物（2 课时）
Electrophilic substitution at carbon, C-Metallated thiophenes and furans, Palladium(0)-catalysed reactions, Oxidation and
reduction.
本节主要讲述呋喃和噻吩类化合物，主要从碳、C 金属噻吩和呋喃的亲电取代、钯催化的反应、氧化和还原进行介绍。
Section 12: 1,2-Azoles and 1,3-Azoles1,2-唑啉和 1,3-唑啉（4 课时）
The 1,2- and 1,3-azoles each contain a nitrogen in an environment analogous to that in pyridine, that is, an imine
nitrogen with a lone pair of electrons in an sp2 orbital in the plane of the ring and not involved in the aromatic
sextet.Each also has another heteroatom in the environment of the nitrogen in pyrrole, the sulfur in thiophene, or the
oxygen in furan, with a pair of electrons in a p orbital orthogonal to the ring and part of the aromatic sextet.
本节主要讲述 1,2-唑啉和 1,3-唑啉，它们都含有类似于吡啶的氮，即在环平面中的 SP2 轨道中含有孤对电子的亚胺氮，而
不参与芳香六烯酸。每个氮原子在 NIT 环境中也有另一个杂原子，从吡咯中的雄酮，噻吩中的硫，或呋喃中的氧，在 p 环
中的一对电子与环和芳香六烯酸的一部分正交。