The Organic Chemistry of Drug Synthesis, Volume 7

Preface xi

1 Open-Chain Compounds 1

1. Peptidomimetic Compounds 2

A. Antiviral Protease Inhibitors 2

1. Human Immunodeficiency Virus 2

2. Human Rhinovirus 9

2. Miscellaneous Peptidomimetic Compounds 11

References 19

2 Alicyclic Compounds 21

1. Monocyclic Compounds 21

A. Prostaglandins 21

B. Antiviral Agents 25

C. Miscellaneous Monocyclic Compounds 29

2. Polycyclic Compounds: Steroids 31

A. 19-Nor Steroids 31

B. Corticosteroid Related Compounds 34

3. Polycyclic Compounds 38

References 40

3 Monocyclic Aromatic Compounds 43

1. Arylcarbonyl Derivatives 43

2. Biphenyls 47

3. Compounds Related to Aniline 50

4. Compounds Related to Arylsulfonic Acids 53

5. Diarylmethanes 58

6. Miscellaneous Monocyclic Aromatic Compounds 60

References 67

4 Carbocyclic Compounds Fused to a Benzene Ring 69

1. Indenes 69

2. Naphthalenes 73

3. Tetrahydronaphthalenes 74

4. Other benzofused carbocyclic compounds 79

References 81

5 Five-Membered Heterocycles 83

1. Compounds with One Heteroatom 83

2. Compounds with Two Heteroatoms 91

A. Oxazole and Isoxazoles 91

B. Imidazoles and a Pyrrazole 94

C. Thiazoles 99

D. Triazoles 103

E. Tetrazoles 109

References 112

6 Six-Membered Heterocycles 115

1. Compounds with One Heteroatom 115

A. Pyridines 115

B. Reduced Pyridines 117

C. Miscellaneous 119

2. Compounds with Two Heteroatoms 121

A. Pyrimidines 121

B. Miscellaneous Six-Membered Heterocycles 133

References 136

7 Five-Membered Heterocycles Fused to One Benzene Ring 139

1. Compounds with One Heteroatom 139

A. Benzofurans 139

B. Indoles 141

C. Indolones 148

D. Miscellaneous Compounds with One Heteroatom 153

2. Five-Membered Rings with Two Heterocyclic Atoms 156

A. Benzimidazoles 156

B. Miscellaneous Compounds 158

References 160

8 Six-Membered Heterocycles Fused to One Benzene Ring 163

1. Compounds with One Heteroatom 163

A. Benzopyrans 163

B. Quinolines and Their Derivatives 167

C. Quinolone Antibacterial Agents 172

2. Compounds with Two Heteroatoms 176

A. Benzoxazines 176

B. Quinazolines 178

C. Miscellaneous Benzo-Fused Heterocycles 184

References 186

9 Bicyclic Fused Heterocycles 189

1. Compounds with Five-Membered Rings Fused to Six-Membered Rings 189

A. Compounds with Two Heteroatoms 189

B. Compounds with Three Heteroatoms 191

C. Compounds with Four Heteroatoms 195

2. Compounds with Two Fused Six-Membered Rings 208

3. Miscellaneous Compounds with Two Fused Heterocyclic Rings: Beta Lactams 213

References 215

10 Polycyclic Fused Heterocycles 217

1. Compounds with Three Fused Rings 217

2. Compounds with Four Fused Rings 228

3. Compounds with Five or More Fused Rings: Camptothecins 230

References 232

Subject Index 233

Cross Index of Biological Activity 241

Cumulative Index 245