Introduction to Heterocyclic Chemistry

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; p-deficient heterocycles; p-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.

Table of Contents:
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