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Introduction 1

Ⅰ．HETEROCYCLIC ANALOGUES OF CYCLOPROPANE 4

1．AZIRINE 4

2．AZIRIDINE 6

A．Introduction 6

B．Physical Properties and Structure 6

C．Chemical Properties 7

D．Derivatives of Aziridine 10

E．Synthetic Methods 13

F．Natural Occurrence and Compounds of Special Interest 14

3．OXIRANE OR ETHYLENE OXIDE 15

A．Introduction 15

B．Physical Properties and Structure 15

C．Chemical Properties 16

D．Derivatives of Oxirane 19

E．Synthetic Methods 22

F．Natural Occurrence and Compounds of Special Interest 24

4．THIIRANE 24

A．Introduction 24

B．Physical Properties and Structure 25

C．Chemical Properties 25

D．Derivatives of Thiirane 27

E．Synthetic Methods 28

5．OXAZIRANE 29

Ⅱ．HETEROCYCLIC ANALOGUES OF CYCLOBUTANE 33

1．AZETIDINE 34

A．Introduction 34

B．Physical Properties and Structure 34

C．Chemical Properties 34

D．Substituted Azetidines 35

E．Synthetic Methods 36

F．Natural Occurrence and Compounds of Special Interest 36

2．AZETIDINONES 36

A．Introduction 36

B．Physical Properties and Structure 37

C．Chemical Properties 37

D．Substituted Derivatives，excluding Penicillin 37

E．Synthetic Methods，excluding Penicillin 38

F．The Penicillins 39

3．OXETANE 42

A．Introduction 42

B．Physical Properties and Structure 42

C．Chemical Properties 43

D．Derivatives of Oxetane 43

E．Synthetic Methods 44

4．OXETANONES 44

A．Introduction 44

B．Physical Properties and Structure 45

C．Chemical Properties 45

D．Derivatives of Oxetanone 46

E．Synthetic Methods 46

5．THIETANE 47

A．Introduction 47

B．Physical Properties and Structure 47

C．Chemical Properties 47

D．Synthetic Methods 48

Ⅲ．HETEROCYCLIC ANALOGUES OF CYCLOPENTADIENE WITH ONE HETEROATOM 50

1．PYRROLE 50

A．Introduction 50

B．Physical Properties and Structure 51

C．Chemical Properties 54

D．Derivatives of Pyrrole 61

E．Synthetic Methods 70

F．Natural Occurrence and Compounds of Special Interest 72

2．FURAN 78

A．Introduction 78

B．Physical Properties and Structure 78

C．Chemical Properties 81

D．Derivatives of Furan 86

E．Synthetic Methods 101

F．Natural Occurrence and Compounds of Special Interest 102

3．THIOPHENE 103

A．Introduction 103

B．Physical Properties and Structure 104

C．Chemical Properties 106

D．Derivatives of Thiophene 110

E．Synthetic Methods 118

F．Natural Occurrence and Compounds of Special Interest 119

4．A SUMMARY COMPARISON OF THE AROMATIC PROPERTIES OF PYRROLE，FURAN，AND THIOPHENE 122

Ⅳ．FUSED RING SYSTEMS INVOLVING PYRROLE，FURAN，AND THIOPHENE RINGS 127

1．INDOLE 127

A．Introduction 127

B．Physical Properties and Structure 128

C．Chemical Properties 129

D．Derivatives of Indole 133

E．Synthetic Methods 140

F．Natural Occurrence and Compounds of Special Interest 142

2．ISOINDOLE 147

3．PYRROCOLINE 149

4．BENZOFURAN 150

A．General Properties of Benzofurans 150

B．Synthetic Methods 152

5．DIBENZOFURAN 152

6．ISOBENZOFURANS 153

7．THIANAPHTHENE AND RELATED COMPOUNDS 154

A．Physical Properties and Structure 154

B．Chemical Properties and Derivatives 154

C．Synthetic Methods 157

D．Compounds of Special Interest 157

Ⅴ．HETEROCYCLIC ANALOGUES OF BENZENE WITH ONE HETEROATOM 160

1．PYRIDINE 160

A．Introduction 160

B．Physical Properties and Structure 161

C．Chemical Properties 163

D．Derivatives of Pyridine 170

E．Synthetic Methods 192

F．Natural Occurrence and Compounds of Special Interest 197

2．PYRYLIUM SALTS AND PYRANS 203

A．Introduction 203

B．Pyrylium Salts 204

C．2-Pyrones 204

D．4-Pyrans and 4-Pyrones 205

E．Reduced Pyrans 207

Ⅵ．HETEROCYCLIC ANALOGUES OF NAPHTHALENE WITH ONE HETEROATOM 210

1．QUINOLINE 211

A．Introduction 211

B．Physical Properties and Structure 211

C．Chemical Properties 213

D．Derivatives of Quinoline 218

E．Synthetic Methods 223

F．Natural Occurrence and Compounds of Special Interest 227

2．ISOQUINOLINE 231

A．Introduction 231

B．Physical Properties and Structure 232

C．Chemical Properties 233

D．Derivatives of Isoquinoline 236

E．Synthetic Methods 237

3．QUINOLIZINE 238

4．ACRIDINE AND PHENANTHRIDINE 240

A．Introduction 240

B．Acridine 241

C．Phenanthridine 244

5．BENZOPYRYLIUM SALTS AND BENZOPYRANS 246

A．Introduction 246

B．The Anthcyanins 246

C．Benz-2-pyrones 251

D．Benz-4-pyrones 252

Ⅶ．COMPOUNDS WITH TWO HETEROATOMS IN A FIVE-MEMBERED RING 259

1．PYRAZOLE AND IMIDAZOLE 260

A．Introduction 260

B．Physical Properties and Structure 260

C．Chemical Properties and Synthetic Methods 262

D．Derivatives of Pyrazole and Imidazole 264

E．Compounds of Special Interest and Natural Occurrence 266

2．ISOXAZOLE AND OXAZOLE 270

A．Introduction 270

B．Physical Properties and Structure 270

C．Chemical Properties and Synthetic Methods 271

D．Derivatives and Compounds of Special Interest 272

3．ISOTHIAZOLE AND THIAZOLE 275

A．Introduction 275

B．Physical Properties and Structure 275

C．Isothiazoles 276

D．Thiazole，Chemical Properties and Synthetic Methods 276

E．Derivatives of Thiazole 277

F．Thiazoles of Natural Occurrence and Special Interest 279

4．DIOXOLE，DIOXOLANE，AND THEIR SULPHUR ANALOGUES 281

Ⅷ．COMPOUNDS WITH TWO HETEROATOMS IN A SIX-MEMBERED RING 285

1．PYRIDAZINE 286

2．PYRIMIDINE 287

A．Introduction 287

B．Physical Properties and Structure 288

C．Chemical Properties of Pyrimidine and its Derivatives 289

D．Synthetic Methods 294

E．Natural Occurrence and Compounds of Special Interest 297

3．PYRAZINES 298

4．OXAZINES AND THIAZINES 301

5．DIOXANES AND THEIR SULPHUR ANALOGUES 303

Ⅸ．SOME COMPOUNDS WITH MORE THAN TWO HETEROATOMS 306

1．PURINES 306

A．Introduction 306

B．The Structure，and Chemical Reactions of Purine and its Simple Derivatives 306

C．Synthetic Methods 310

D．Purines of Special Interest 311

2．PTERIDINES 316

3．TRIAZINES 320

4．SYDNONES 321

Compound Index 323

Subject Index 338