1. Structure, Properties, and Reactivity of Heterocycles
Using carbocyclic rings as a common point of reference, the effects of heteroatom substitution on the structure, properties, and reactivity of heterocycles will be discussed.  Heterocyclic compounds will be grouped into three categories:  (1) pi-Deficient heteroaromatic compounds; (2) pi-Excessive heteroaromatic compounds; (3) Nonaromatic heterocyclic compounds.

¥ Aim:  To allow chemists to make predictions about the reactivity and properties of unfamiliar heterocycles based on structure.

2. General Aspects of Heterocyclic Ring Synthesis

Heterocyclic ring syntheses will be grouped into three broad categories:  (1) Cyclization processes; (2) Concerted cycloaddition reactions; (3) Modification of existing rings.  The first two categories will be emphasized to the greatest extent. General strategies for retrosynthetic analysis will be presented.

¥ Aim:  To allow chemists to propose a reasonable synthetic approach to unfamiliar heterocycles based on general retrosynthetic concepts.

3. Specific Heterocyclic Ring Syntheses

An overview of some of the most useful modern methods for the synthesis of specific heterocycles will be presented.  References to more classical methods will be provided.

¥ Aim:  To provide the chemist with specific knowledge of heterocyclic synthetic approaches, and to reinforce the application of the general synthetic concepts learned in Section 2 above.

4. Heterocycles in Organic Synthesis

The use of heterocycles as intermediates for organic synthesis will be covered.

¥ Aim:  To demonstrate the role of heterocyclic compounds in the broader realm of organic synthesis.  This section will also further illustrate the reactivity patterns of heterocyclic compounds.

5. Asymmetric Synthesis

The growing importance of chiral, nonracemic heterocycles in medical and agricultural applications necessitates an overview of methods for the assembly of enantiomerically pure heterocycles. Heterocyclizations that introduce asymmetry will be covered.

¥ Aim:  To provide an overview of the asymmetric synthetic methods most useful to heterocyclic chemists.

6. Retrieval of Heterocyclic Chemical Information

In addition to the extensive information on specific aspects of heterocyclic chemistry that will provided in the notes throughout the course, a brief tour of the important sources of information in heterocyclic chemistry will also be supplied.   An easy-to-use Heterocyclic Chemistry Database is available for a slight supplement which will allow rapid retrieval of leading references to all aspects of heterocyclic chemistry.  The database runs on common desktop PC's, and contains 100,000 references.  To see a demo version of the ChemKey Database, click here.

¥ Aim:  To provide the chemist with practical information on finding heterocyclic chemical information in an efficient manner.

7. Nomenclature of Heterocyclic Compounds

Brief coverage of the basics of Trivial, Hantzsch-Widman, and Replacement methods of nomenclature will be covered in handout form.