Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals

Louis D. Quin, John A. Tyrell

ISBN: 9788126598076

344 pages

Exclusively distributed by CBS Publishers & Distributors



This book explains the essentials of heterocyclic chemistry. It is based on a course the authors teach and is derived from the lectures given in this course which emphasizes biological aspects. After a necessary grounding in nomenclature, chapters discuss the occurrence and importance of heterocycles in nature and in synthetic pharmaceuticals. Next, synthetic methods are presented by describing particular reactions used to construct heterocycles. Because students rarely remember such reactions from a basic course, the authors provide a brief review as each reaction type is presented. After this background in synthesis, the authors present special properties of various aromatic heterocyclic systems.




Chapter 1 The Scope Of The Field Of Heterocyclic Chemistry.


Chapter 2 Common Ring Systems And The Naming Of Heterocyclic Compounds.

2.1. General.

2.2. Naming Simple Monocyclic Compounds.

2.3. Handling the "Extra Hydrogen".

2.4. Substituted Monocyclic Compounds.

2.5. Rings With More Than One Heteroatom.

2.6. Bicyclic Compounds.

2.7. Multicyclic Systems.

2.8. The Replacement Nomenclature System.

2.9. Saturated Bridged Ring Systems.


Chapter 3 Nature As A Source Of Heterocyclic Compounds.

3.1. General.

3.2. Naturally Occurring Nitrogen Heterocyclic Compounds.

3.3. Oxygen Compounds.

3.4. Sulfur and Phosphorus Heterocyclic Compounds in Nature.


Chapter 4 Principles Of Synthesis Of Aromatic Heterocycles By Intramolecular Cyclization.

4.1. General.

4.2. Some of the Classic Synthetic Methods.

4.3. Cyclizations Involving Metallic Complexes as Catalysts.

4.4. Cyclizations with Radical Intermediates.

4.5. Cyclizations by Intramolecular Wittig Reactions.

4.6. Synthesis of Heterocycles by the Alkene Metathesis Reaction.


Chapter 5 Synthesis Of Heterocyclic Systems By Cycloaddition Reactions.

5.1. The Diels--Alder Reaction.

5.2. Dipolar Cycloadditions.

5.3. [2 + 2] Cycloadditions.


Chapter 6 Aromaticity And Other Special Properties Of Heterocycles: Pi-Deficient Ring Systems.

6.1. General.

6.2. Review of the Aromaticity of Benzene.

6.3. Pi-Deficient Aromatic Heterocycles.


Chapter 7 Aromaticity And Other Special Properties Of Heterocycles: Pi-Excessive Ring Systems And Mesoionic Ring Systems.

7.1. Pi-Excessive Aromatic Heterocycles.

7.2. Mesoionic Heterocycles.


Chapter 8 The Importance Of Heterocycles In Medicine.

8.1. General.

8.2. Historical.

8.3. Pyridines.

8.4. Indoles.

8.5. Quinolines.

8.6. Azepines.

8.7. Pyrimidines.

8.8. Concluding Remarks.


Chapter 9 Synthetic Methods For Some Prominent Heterocyclic Families: Examples Of Pharmaceuticals Synthesis.

9.1. Scope of the Chapter.

9.2. Pyrroles.

9.3. Furans.

9.4. Thiophenes.

9.5. 1,3-Thiazoles.

9.6. 1,3-Oxazoles.

9.7. Imidazoles.

9.8. Pyrazoles.

9.9. 1,2,4-Triazoles.

9.10. Tetrazoles.

9.11. 1,3,4-Thiadiazoles and other 5-Membered Systems.

9.12. Indole.

9.13. Pyridines.

9.14. Quinolines and Isoquinolines.

9.15. Benzodiazepines.

9.16. Pyrimidines.

9.17. Fused Pyrimidines: Purines and Pteridines.

9.18. 1,3,5-Triazines.

9.19. Multicyclic Compounds.


Chapter 10 Geometric And Stereochemical Aspects Of Nonaromatic Heterocycles.

10.1. General.

10.2. Special Properties of Three-Membered Rings.

10.3. Closing Heterocyclic Rings: Baldwin's Rules.

10.4. Conformations of Heterocyclic Rings.

10.5. Chirality Effects on Biological Properties of Heterocycles.


Chapter 11 Synthetic Heterocyclic Compounds In Agricultural And Other Applications.

11.1. Heterocyclic Agrochemicals.

11.2. Applications of Heterocyclic Compounds in Commercial Fields.



Appendix Unified Aromaticity Indices (Ia) Of Bird.