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

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Overview

  • Heterocyclic chemistry is of prime importance as a sub-discipline of Organic Chemistry, as millions of heterocyclic compounds are known with more being synthesized regularly
  • Introduces students to heterocyclic chemistry and synthesis with practical examples of applied methodology
  • Emphasizes natural product and pharmaceutical applications
  • Provides graduate students and researchers in the pharmaceutical and related sciences with a background in the field
  • Includes problem sets with several chapters
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Editorial Reviews

From the Publisher
"Provides graduate students and researchers in the pharmaceutical and related sciences with a background in the field." (Trading Charts, 22 February 2011)
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Product Details

  • ISBN-13: 9780470566695
  • Publisher: Wiley
  • Publication date: 8/9/2010
  • Edition description: New Edition
  • Edition number: 1
  • Pages: 327
  • Product dimensions: 6.00 (w) x 9.10 (h) x 1.00 (d)

Meet the Author

LOUIS D. QUIN, PhD, is an Adjunct Professor at the University of North Carolina Wilmington. Dr. Quin began his academic career in 1956 with the Department of Chemistry at Duke University, serving as department chairman from 1970 to 1976. After retiring from Duke, he went to the University of Massachusetts Amherst to head up its Chemistry Department, retiring in 1996. Dr. Quin has written 250 research papers and written or co-edited eight books on the subject of organophosphorus chemistry.

JOHN A. TYRELL, PhD, is Visiting Scientist in the Department of Chemistry and Bio-chemistry at the University of North Carolina Wilmington, where he teaches Fundamentals of Heterocyclic Chemistry among other courses. Dr. Tyrell holds sixty-eight patents and has more than twenty years of industrial research experience, much of it focused on heterocyclic chemistry research at Lederle Laboratories, General Electric Plastics, and OxyChem.

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Table of Contents

Preface

Acknowledgment

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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