Nomenclature and Numbering System 1
Ⅰ．Acridines 9
1．Methods of preparation of Acridines 9
A．Preparation of Acridines from Acridones or 9-Chloro-acridines 9
B．The Bernthsen Reaction 19
C．Preparation of Acridines from m-Phenylenediamines and Formic(or Oxalic Acid) 25
D．Acridines and Acridans from Aromatic Amines and Alde-hydes and Similar Syntheses 34
E．Cyclisstion of Diphenylamine-2-aldehydes and Ketones 37
F．Other Methods of Preparing Acridines 44
2．Acridine 51
A．Historical Introduction and the Formulation of Acridine 51
B．General Properties of Acridine 54
C．Chemical Properties of Acridine 56
3．Substituted Acridines 59
A．Nitroacridines 60
B．Halogen Substituted Acridines 61
C．Acridine-N-oxides 64
D．Hydroxyacridines 65
E．Alkoxy and Aryloxyacridines 66
F．Alkyl and Arylacridines 68
G．Acridine Aldehydes and Ketones 74
H．Cyanoacridines 76
I．Acridine Carboxylic Acids 77
Ⅱ．Aminoacridines 79
1．Basic Strengths and Solution Properties 79
2．1-,2-,3- and 4-Aminoacridines 83
3．9-Aminoacridines 85
A．Preparation 85
B．Properties 90
4．Synthesis and Properties of Atebrin(Quinacrine) 94
5．Aminoalkyl and Aminoarylacridines 97
6．Diamino and Triaminoacridines 101
Ⅲ．Acridones 105
1．Preparation of Acridones from Diphenylamine-2-carboxylic Acids 105
A．Cyclisations with Phosphorus Oxychloride 105
B．Cyclisations with Sulphuric Acid 110
C．Cyclisations with other Reagents 111
D．Alternative Cyclisations 113
E．Cyclisation of N-Substituted Diphenylamine-2-carboxylic Acids 117
F．Cyclisation Failures and Difficult Cyclisations 118
G．Mechanism of the Cyclisation 120
2．Preparation of Diphenylamine-2-carboxylic Acids 148
A．The Ullmann Reaction 148
B．Other Methods of Preparing Diphenylamine-2-carboxylic Acids 161
3．Other Methods of Acridone Synthesis 165
A．Rearrangement of Phenylanthranils to Acridones 166
B．Oxidation of Acridines 168
C．Miscellaneous Methods of Acridone Synthesis 169
4．Synthesis of N-substituted Acridones 170
5．Structure,Properties and Reactions of Acridone and Its Derivatives 173
A．General Properties and Structure 173
B．Chemical Properties of Acridone 175
C．Substituted Acridones 180
6．9(10)-Acridinethione and 9(10)-Acridineselenone 192
A．9(10)-Acridinethione 192
B．9(10)-Acridineselenone 198
Ⅳ．The Acridine Alkalolds 199
1．Alkaloids of Melicope fareana F．Muell 199
A．Isolation 199
B．General Properties,Structure and Synthesis of Melicopicine 200
C．The nor Alkaloids 203
D．Action of Alkali Metal Alkoxides on the Alkaloids 207
E．Acid Degradation Products 214
2．Alkaloids of Evodia xanthoxyloides F．Muell 217
A．Isolation 217
B．Evoxanthine 219
C．Evoxanthidine and Xanthevodine 221
D．Xanthoxoline 222
3．Alkaloids of Acronychia Baueri Schott 224
A．Isolation 224
B．Acronycine 225
4．Biosynthesis of the Alkaloids 232
Ⅴ．Acridinium Salts and Reduced Acridines 234
1．Acridinum Salts 234
A．Methods of Preparation 234
B．General Properties and Reactions 237
2．Acridans 249
A．Methods of Preparation 249
B．Properties and Reactions of Aeridans 257
3．More Highly Reduced Acridines 262
A．Tetrahydroacridines 262
B．Tetrahydroacridones 271
C．Other Highly Reduced Acridines 273
Ⅵ．Biacridines 277
1．9,9＇-Biacridines 277
A．9,9＇-Biacridine 277
B．Δ9,9＇-Biacridans 278
C．10,10＇-Dialkyl-9,9＇-biacridinium Salts 280
D．9,9＇-Biacridans 285
2．9,10＇-Biacridines 286
3．10,10＇-Biacridines 287
4．Some Stereochemical Considerations 287
Ⅶ．Visible and Ultraviolet Absorption Spectra of Acridine and its Derivatives．＆By L．E．ORGEL 289
1．Acridine 289
2．Aminoacridines 290
3．Hydroxyacridines,Acridone and 9(10)-Acridinethione 298
4．Acridans 300
5．Theoretical Considerations 303
6．Appendix:Infrared Absorption Spectra 304
Ⅷ．Benzacridines,Condensed Acridines and Acridine Dyes 307
1．Benzacridines and Condensed Acridines 307
A．Benzacridines and Condensed Acridines with Four Rings 307
B．Dibenzacridines and Condensed Acridines with Five Rings 312
C．Condensed Acridines with Six or More Rings 321
2．Acridine Dyes 325
A．Simple Acridine Dyes 325
B．Simple Acridone Dyes 328
C．Complex Acridine and Aeridone Vat Dyes 328
Ⅸ．Biologically Active Acridines 339
1．General Historical Introduction 339
2．Acridine Antibacterials 340
A．Proflavine,or 3,6-Diaminoacridine 341
B．Acriflavine,or 3,6-Diamino-10-methylacridinium Chloride 344
C．9-Aminoacridine 346
D．Other Acridines Used as Antibacterials 348
E．Relation between Structure and Antibacterial Activity of Acridines 350
F．Possible Mechanisms of the Antibacterial Action of Acridines and Related Topics 358
3．Acridine Antimalarials 362
A．The Malaria Cycle and the Screening of Potential Anti-malarials 362
B．Acridine Antimalarials 365
C．Atebrin,or Quinacrine 373
D．Antimalarial Activity and Chemical Constitution of Acridines 377
E．Mechanism of Action of Acridine Antimalarials and Related Topics 380
4．Other Biologically Active Acridines 382
A．Acridines and Cancer 382
B．Miscellaneous Biological Data 386
Index 391