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Introduction to Heterocyclic Chemistry

Introduction to Heterocyclic Chemistry

Peter A. Jacobi

ISBN: 978-1-119-41769-9

Sep 2018

272 pages


A unique approach to a core topic in organic chemistry presented by an experienced teacher to students and professionals

Heterocyclic rings are present in the majority of known natural products, contributing to enormous structural diversity. In addition, they often possess significant biological activity. Medicinal chemists have embraced this last property in designing most of the small molecule drugs in use today. This book offers readers a fundamental understanding of the basics of heterocyclic chemistry and their occurrence in natural products such as amino acids, DNA, vitamins, and antibiotics. Based on class lectures that the author has developed over more than 40 years of teaching, it focuses on the chemistry of such heterocyclic substances and how they differ from carbocyclic systems.

Introductory Heterocyclic Chemistry offers in-depth chapters covering naturally occurring heterocycles; properties of aromatic heterocycles; π-deficient heterocycles; π-excessive heterocycles; and ring transformations of heterocycles. It then offers an overview of 1,3-dipolar cycloadditions before finishing up with a back-to-basics section on nitriles and amidines.

  • Presents a conversational approach to a fundamental topic in organic chemistry teaching 
  • Offers a unique look at this core organic chemistry topic via important naturally occurring and/or biologically active heterocycles 
  • Based on the author's many years of class lectures for teaching at the undergraduate and graduate level as well as pharmaceutical-industry courses 
  • Clear, concise, and accessible for advanced students of chemistry to gain a fundamental understanding of the basics of heterocyclic chemistry 

Introductory Heterocyclic Chemistry is an excellent text for undergraduate and graduate students as well as chemists in industrial environments in chemistry, pharmacy, medicinal chemistry, and biology.

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Preface ix

Acknowledgments xi

1 Some Biologically Important Heterocycles of Nature 1

1.1 Vitamins 3

1.2 Antibiotics and Tetrapyrroles 8

References 10

2 Orbitals and Aromaticity; Chemical Reactivity 11

References 15

3 A Prelude to Synthesis 17

References 21

4 π‐Deficient Heterocycles: Some Physical Properties 23

References 25

5 π‐Deficient Heterocycles: De Novo Syntheses 27

5.1 De Novo Syntheses, Pyrimidines 32

5.2 Fused‐Ring Systems, Quinolines 33

5.2.1 Isoquinolines 34

References 37

6 π‐Deficient Heterocycles: Introduction of New Substituents: Nucleophilic Substitution 39

References 48

7 π‐Deficient Heterocycles: Introduction of New Substituents: Heterocyclic N‐Oxides 49

7.1 Further Reactions of N‐Oxides 61

References 73

8 π‐Deficient Heterocycles: Introduction of New Substituents: Quinolines and Isoquinolines 75

References 86

9 π‐Deficient Heterocycles: Manipulation of Existing Substituents 89

9.1 Summary 103

References 105

10 π‐Excessive Heterocycles: General Properties 107

References 114

11 π‐Excessive Heterocycles: De Novo Syntheses 115

11.1 Synthesis of 1,3‐Azoles 127

11.2 Synthesis of 1,2‐Azoles 131

11.3 Fischer Indole Synthesis 133

References 136

12 π‐Excessive Heterocycles: Introduction of New Substituents 139

References 153

13 Ring Transformations of π‐Excessive Heterocycles: Diels‐Alder Reactions 157

References 175

14 Heterocycles as Synthons 177

References 205

15 1,3‐Dipolar Cycloadditions—An Overview 207

References 234

16 Back to Basics 239

References 245

17 A Brief Synopsis 247

Index 251