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Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals / Edition 1
     

Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals / Edition 1

by Louis D. Quin, John A. Tyrell
 

ISBN-10: 0470566698

ISBN-13: 9780470566695

Pub. Date: 08/09/2010

Publisher: Wiley

Based on popular courses taught by the two authors, Fundamentals of Heterocyclic Chemistry enables students to master the basics of heterocyclic chemistry and synthesis. The text features detailed examples throughout and a clear, straightforward approach, making it easy to grasp a vast, complex field. Moreover, with its emphasis on the biological uses of

Overview

Based on popular courses taught by the two authors, Fundamentals of Heterocyclic Chemistry enables students to master the basics of heterocyclic chemistry and synthesis. The text features detailed examples throughout and a clear, straightforward approach, making it easy to grasp a vast, complex field. Moreover, with its emphasis on the biological uses of heterocyclic compounds, the text enables students to learn a variety of practical applications in natural products and pharmaceutical research.

Following an introduction to basic nomenclature, Fundamentals of Heterocyclic Chemistry explores the importance of heterocycles in nature and in synthetic pharmaceuticals. Next, synthetic methods are introduced with detailed descriptions of specific reactions used to construct heterocycles. The authors have provided a brief review of each reaction presented.

The text moves on to explore special properties of various aromatic heterocyclic systems. Next, the authors explain the synthesis of some important families of heterocycles, using plenty of examples for illustration, mostly from the field of pharmaceutics. The final chapter covers saturated heterocycles, with an emphasis on stereochemical properties.

This text is ideal for undergraduate and graduate students in organic chemistry as well as pharmaceutical and medicinal chemistry. Most of the chapters include problem sets, enabling students to test and build their knowledge of key concepts by applying principles of heterocyclic chemistry to solve real problems.

Product Details

ISBN-13:
9780470566695
Publisher:
Wiley
Publication date:
08/09/2010
Pages:
344
Product dimensions:
6.00(w) x 9.10(h) x 1.00(d)

Table of Contents

Preface xiii

Acknowledgment xv

Chapter 1 The Scope of the Field of Heterocyclic Chemistry 1

References 5

Appendix 6

Chapter 2 Common Ring Systems and the Naming of Heterocyclic Compounds 8

2.1 General 8

2.2 Naming Simple Monocyclic Compounds 11

2.3 Handling the "Extra Hydrogen" 13

2.4 Substituted Monocyclic Compounds 14

2.5 Rings With More Than One Heteroatom 15

2.6 Bicyclic Compounds 17

2.7 Multicyclic Systems 19

2.8 The Replacement Nomenclature System 21

2.9 Saturated Bridged Ring Systems 22

References 23

Review Exercises 23

Chapter 3 Nature as A Source of Heterocyclic Compounds 29

3.1 General 29

3.2 Naturally Occurring Nitrogen Heterocyclic Compounds 30

3.3 Oxygen Compounds 51

3.4 Sulfur and Phosphorus Heterocyclic Compounds in Nature 55

References 57

Chapter 4 Principles of Synthesis of Aromatic Heterocycles by Intramolecular Cyclization 58

4.1 General 58

4.2 Some of the Classic Synthetic Methods 60

4.3 Cyclizations Involving Metallic Complexes as Catalysts 78

4.4 Cyclizations with Radical Intermediates 82

4.5 Cyclizations by Intramolecular Wittig Reactions 84

4.6 Synthesis of Heterocycles by the Alkene Metathesis Reaction 89

References 91

Review Exercises 92

Chapter 5 Synthesis of Heterocyclic Systems By Cycloaddition Reactions 98

5.1 The Diels-Alder Reaction 98

5.2 Dipolar Cycloadditions 112

5.3 [2 + 2] Cycloadditions 122

References 125

Review Exercises 126

Chapter 6 Aromaticity and Other Special Properties of Heterocycles: Pi-Deficient Ring Systems 131

6.1 General 131

6.2 Review of the Aromaticity of Benzene 132

6.3 Pi-Deficient Aromatic Heterocycles 138

References 165

Review Exercises 166

Chapter 7 Aromaticity And Other Special Properties of Heterocycles: Pi-Excessive Ring Systems and Mesoionic Ring Systems 170

7.1 Pi-Excessive Aromatic Heterocycles 170

7.2 Mesoionic Heterocycles 189

References 191

Review Exercises 192

Chapter 8 The Importance of Heterocycles in Medicine 196

8.1 General 196

8.2 Historical 197

8.3 Pyridines 204

8.4 Indoles 207

8.5 Quinolines 209

8.6 Azepines 211

8.7 Pyrimidines 213

8.8 Concluding Remarks 217

References 219

Chapter 9 Synthetic Methods for Some Prominent Heterocyclic Families: Examples of Pharmaceuticals Synthesis 221

9.1 Scope of the Chapter 221

9.2 Pyrroles 222

9.3 Furans 225

9.4 Thiophenes 227

9.5 1,3-Thiazoles 228

9.6 1,3-Oxazoles 233

9.7 Imidazoles 235

9.8 Pyrazoles 239

9.9 1,2,4-Triazoles 239

9.10 Tetrazoles 240

9.11 1,3,4-Thiadiazoles and other 5-Membered Systems 241

9.12 Indole 242

9.13 Pyridines 246

9.14 Quinolines and Isoquinolines 250

9.15 Benzodiazepines 254

9.16 Pyrimidines 256

9.17 Fused Pyrimidines: Purines and Pteridines 265

9.18 1,3,5-Triazines 267

9.19 Multicyclic Compounds 270

References 272

Review Exercises 273

Chapter 10 Geometric and Stereochemical Aspects of Nonaromatic Heterocycles 280

10.1 General 280

10.2 Special Properties of Three-Membered Rings 282

10.3 Closing Heterocyclic Rings: Baldwin's Rules 287

10.4 Conformations of Heterocyclic Rings 290

10.5 Chirality Effects on Biological Properties of Heterocycles 298

References 302

Review Exercises 303

Chapter 11 Synthetic Heterocyclic Compounds in Agricultural and Other Applications 306

11.1 Heterocyclic Agrochemicals 306

11.2 Applications of Heterocyclic Compounds in Commercial Fields 316

References 319

Appendix: Unified Aromaticity Indices (IA) of Bird 321

Index 323

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