Introduction to Heterocyclic Chemistry (eBook)

PETER A. JACOBI, PHD, received his B.S. degree in Chemistry from the University of New Hampshire (1967), and his Ph.D. in Organic Chemistry from Princeton University (1973). After two years at Harvard as a postdoctoral fellow, he joined the faculty of Wesleyan University (1975). In the fall of 1997 he moved from Wesleyan to Dartmouth, where in 2004 he was appointed the New Hampshire Professor of Chemistry, a position he held until 2013. Dr. Jacobi is the recipient of numerous awards including the American Cyanamid Company Award for "Advancement of the Art and Science of Synthesis" (1985); the Connecticut Valley ACS Award for "Outstanding Contributions to Chemistry" (1988); and the Caleb T. Winchester Award for "Excellence as a Scholar-Teacher" (1996). In 2010 he was elected as a Fellow of the American Chemical Society. He is the author of nearly 100 publications in the general area of heterocyclic chemistry, in particular as applied to natural product synthesis.

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 pi-Deficient Heterocycles: Some Physical Properties 23

References 25

5 pi-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 pi-Deficient Heterocycles: Introduction of New Substituents: Nucleophilic Substitution 39

References 48

7 pi-Deficient Heterocycles: Introduction of New Substituents: Heterocyclic N-Oxides 49

7.1 Further Reactions of N-Oxides 61

References 73

8 pi-Deficient Heterocycles: Introduction of New Substituents: Quinolines and Isoquinolines 75

References 86

9 pi-Deficient Heterocycles: Manipulation of Existing Substituents 89

9.1 Summary 103

References 105

10 pi-Excessive Heterocycles: General Properties 107

References 114

11 pi-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 pi-Excessive Heterocycles: Introduction of New Substituents 139

References 153

13 Ring Transformations of pi-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