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Introduction1

Ⅰ．HETEROCYCLIC ANALOGUES OF CYCLOPROPANE4

1．AZIRINE4

2．AZIRIDINE6

A．Introduction6

B．Physical Properties and Structure6

C．Chemical Properties7

D．Derivatives of Aziridine10

E．Synthetic Methods13

F．Natural Occurrence and Compounds of Special Interest14

3．OXIRANE OR ETHYLENE OXIDE15

A．Introduction15

B．Physical Properties and Structure15

C．Chemical Properties16

D．Derivatives of Oxirane19

E．Synthetic Methods22

F．Natural Occurrence and Compounds of Special Interest24

4．THIIRANE24

A．Introduction24

B．Physical Properties and Structure25

C．Chemical Properties25

D．Derivatives of Thiirane27

E．Synthetic Methods28

5．OXAZIRANE29

Ⅱ．HETEROCYCLIC ANALOGUES OF CYCLOBUTANE33

1．AZETIDINE34

A．Introduction34

B．Physical Properties and Structure34

C．Chemical Properties34

D．Substituted Azetidines35

E．Synthetic Methods36

F．Natural Occurrence and Compounds of Special Interest36

2．AZETIDINONES36

A．Introduction36

B．Physical Properties and Structure37

C．Chemical Properties37

D．Substituted Derivatives，excluding Penicillin37

E．Synthetic Methods，excluding Penicillin38

F．The Penicillins39

3．OXETANE42

A．Introduction42

B．Physical Properties and Structure42

C．Chemical Properties43

D．Derivatives of Oxetane43

E．Synthetic Methods44

4．OXETANONES44

A．Introduction44

B．Physical Properties and Structure45

C．Chemical Properties45

D．Derivatives of Oxetanone46

E．Synthetic Methods46

5．THIETANE47

A．Introduction47

B．Physical Properties and Structure47

C．Chemical Properties47

D．Synthetic Methods48

Ⅲ．HETEROCYCLIC ANALOGUES OF CYCLOPENTADIENE WITH ONE HETEROATOM50

1．PYRROLE50

A．Introduction50

B．Physical Properties and Structure51

C．Chemical Properties54

D．Derivatives of Pyrrole61

E．Synthetic Methods70

F．Natural Occurrence and Compounds of Special Interest72

2．FURAN78

A．Introduction78

B．Physical Properties and Structure78

C．Chemical Properties81

D．Derivatives of Furan86

E．Synthetic Methods101

F．Natural Occurrence and Compounds of Special Interest102

3．THIOPHENE103

A．Introduction103

B．Physical Properties and Structure104

C．Chemical Properties106

D．Derivatives of Thiophene110

E．Synthetic Methods118

F．Natural Occurrence and Compounds of Special Interest119

4．A SUMMARY COMPARISON OF THE AROMATIC PROPERTIES OF PYRROLE，FURAN，AND THIOPHENE122

Ⅳ．FUSED RING SYSTEMS INVOLVING PYRROLE，FURAN，AND THIOPHENE RINGS127

1．INDOLE127

A．Introduction127

B．Physical Properties and Structure128

C．Chemical Properties129

D．Derivatives of Indole133

E．Synthetic Methods140

F．Natural Occurrence and Compounds of Special Interest142

2．ISOINDOLE147

3．PYRROCOLINE149

4．BENZOFURAN150

A．General Properties of Benzofurans150

B．Synthetic Methods152

5．DIBENZOFURAN152

6．ISOBENZOFURANS153

7．THIANAPHTHENE AND RELATED COMPOUNDS154

A．Physical Properties and Structure154

B．Chemical Properties and Derivatives154

C．Synthetic Methods157

D．Compounds of Special Interest157

Ⅴ．HETEROCYCLIC ANALOGUES OF BENZENE WITH ONE HETEROATOM160

1．PYRIDINE160

A．Introduction160

B．Physical Properties and Structure161

C．Chemical Properties163

D．Derivatives of Pyridine170

E．Synthetic Methods192

F．Natural Occurrence and Compounds of Special Interest197

2．PYRYLIUM SALTS AND PYRANS203

A．Introduction203

B．Pyrylium Salts204

C．2-Pyrones204

D．4-Pyrans and 4-Pyrones205

E．Reduced Pyrans207

Ⅵ．HETEROCYCLIC ANALOGUES OF NAPHTHALENE WITH ONE HETEROATOM210

1．QUINOLINE211

A．Introduction211

B．Physical Properties and Structure211

C．Chemical Properties213

D．Derivatives of Quinoline218

E．Synthetic Methods223

F．Natural Occurrence and Compounds of Special Interest227

2．ISOQUINOLINE231

A．Introduction231

B．Physical Properties and Structure232

C．Chemical Properties233

D．Derivatives of Isoquinoline236

E．Synthetic Methods237

3．QUINOLIZINE238

4．ACRIDINE AND PHENANTHRIDINE240

A．Introduction240

B．Acridine241

C．Phenanthridine244

5．BENZOPYRYLIUM SALTS AND BENZOPYRANS246

A．Introduction246

B．The Anthcyanins246

C．Benz-2-pyrones251

D．Benz-4-pyrones252

Ⅶ．COMPOUNDS WITH TWO HETEROATOMS IN A FIVE-MEMBERED RING259

1．PYRAZOLE AND IMIDAZOLE260

A．Introduction260

B．Physical Properties and Structure260

C．Chemical Properties and Synthetic Methods262

D．Derivatives of Pyrazole and Imidazole264

E．Compounds of Special Interest and Natural Occurrence266

2．ISOXAZOLE AND OXAZOLE270

A．Introduction270

B．Physical Properties and Structure270

C．Chemical Properties and Synthetic Methods271

D．Derivatives and Compounds of Special Interest272

3．ISOTHIAZOLE AND THIAZOLE275

A．Introduction275

B．Physical Properties and Structure275

C．Isothiazoles276

D．Thiazole，Chemical Properties and Synthetic Methods276

E．Derivatives of Thiazole277

F．Thiazoles of Natural Occurrence and Special Interest279

4．DIOXOLE，DIOXOLANE，AND THEIR SULPHUR ANALOGUES281

Ⅷ．COMPOUNDS WITH TWO HETEROATOMS IN A SIX-MEMBERED RING285

1．PYRIDAZINE286

2．PYRIMIDINE287

A．Introduction287

B．Physical Properties and Structure288

C．Chemical Properties of Pyrimidine and its Derivatives289

D．Synthetic Methods294

E．Natural Occurrence and Compounds of Special Interest297

3．PYRAZINES298

4．OXAZINES AND THIAZINES301

5．DIOXANES AND THEIR SULPHUR ANALOGUES303

Ⅸ．SOME COMPOUNDS WITH MORE THAN TWO HETEROATOMS306

1．PURINES306

A．Introduction306

B．The Structure，and Chemical Reactions of Purine and its Simple Derivatives306

C．Synthetic Methods310

D．Purines of Special Interest311

2．PTERIDINES316

3．TRIAZINES320

4．SYDNONES321

Compound Index323

Subject Index338