Six Membered Heterocyclic Nitrogen Compounds with Three Condensed Rings, Volume 12

Preface vii

Introduction 1
By C. V. Wilson

Mechanism of Ring Closure 7
By G. A. Reynolds

I. Azaanthracenes 14
By C. V. Wilson

1. Monoazaanthracenes 14

A. 1-Azaanthracene 14

B. 2-Azaanthracene 55

2. Diazaanthracenes 72

A. 1,2-Diazaanthracene 73

B. 1,3-Diazaanthracene 74

C. 1,4-Diazaanthracene 79

D. 1,5-Diazaanthracene 81

E. 1,8-Diazaanthracene 85

F. 1,9-Diazaanthracene 91

G. 1,10-Diazaanthracene 98

H. 2,3-Diazaanthracene 101

I. 2,6-Diazaanthracene 103

J. 2,9-Diazaanthracene 103

K. 2,10-Diazaanthracene 104

3. Triazaanthracenes 118

Nomenclature 118

A. 1,2,3-Triazaanthracene 118

B. 1,2,4-Triazaanthracene 119

C. 1,3,9-Triazaanthracene 119

D. 1,8,9-Triazaanthracene 122

E. 1,9,10-Triazaanthracene 123

F. 2,3,9-Triazaanthracene 124

G. 2,9,10-Triazaanthracene 125

4. Tetrazaanthracenes 130

Nomenclature 130

A. 1,2,7,8-Tetrazaanthracene 130

B. 1,3,5,7-Tetrazaanthracene 131

C. 1,3,6,8-Tetrazaanthracene 133

D. 1,4,5,8-Tetrazaanthracene 135

E. 1,4,9,10-Tetrazaanthracene 136

F. 2,3,6,7-Tetrazaanthracene 139

G. 2,7,9,10-Tetrazaanthracenc 141

5. Pentazaanthracenes 147

A. 1,3,8,9,10-Pentazaanthracene 147

6. Hexazaanthracenes 151

A. 1,3,6,8 9,10-Hexazaanthracene 151

B. 1,3,5,7,9,10-Hexazaanthracene 157

C. 1,2,4,5,7,8-Hexazaanthracene 158

References 161

II. Azaphenanthrenes 165
By John R. Thirtle

1. Monoazaphenanthrenes 165

A. I-Azaphenanthrene 165

B. 2-Azaphenanthrene 206

C. 3-Azaphenanthrene 209

References 211

III. 4-Azaphenanthrenes 216
By J. A. Van Allan

A. Nomenclature 216

B. Synthesis of the 4-Azaphenanthrene System 217

C. Derivatives 237

D. Reactions of the Ring 243

E. Properties 254

F. Uses 255

References 266

IV. 5-Azaphenanthrenes 271
By J. A. Van Allan

A. Nomenclature 271

B. Methods of Synthesis 272

C. Phenanthridinium Salts 287

D. Aminoalkylphenanthridines 292

E. Plant Alkaloids of the Phenanthridine Group 294

F. Reactions of Phenanthridine Derivatives 297

G. Oxidation 301

H. Direct Substitution 302

I. Properties 303

J. Tables 305

References 316

V. Diazaphenanthrenes (except Phenanthrolines) 320
By John R.Thirtle

A. 1,2-Diazaphenanthrene 320

B. 1,3-Diazaphenanthrene 322

C. 1,4-Diazaphenanthrene 328

D. 1,6-Diazaphenanthrene 356

E. 1,8-Diazaphenanthrene 358

F. 2,3-Diazaphenanthrene 359

G. 2,4-Diazaphenanthrene 360

H. 3,5-Diazaphcnanthrene 362

I. 3,6-Diazaphenanthrene 364

J. 3,8-Diazaphenanthrene 369

K. 4,5-Diazaphenanthrene 370

L. 5,6-Diazaphenanthrene 371

References 382

VI. 1,10-, 1,7-, and 4,7-Diazaphenanthrenes 386
By Bruce Graham

Introduction 386

A. 1,10-Diazaphenanthrene 387

B. 1,7-Diazaphenanthrene 409

C. 4,7-Diazaphenanthrene 435

References 454

VII. Other Polyazaphenanthrenes 457
By John R. Thirtle

A. 1,2,3-Triazaphenanthrene 457

B. 1,2,4-Triazaphenanthrene 458

C. 1,2,10-Triazaphenanthrene 464

D. 1,3,4-Triazaphenanthrene 465

E. 1,3,7-Triazaphenanthrene 470

F. 1,4,7-Triazaphenanthrene 472

G. 1,5,7-Triazaphenanthrene 474

H. 1,6,7-Triazaphenanthrene 474

I. 2,4,6-Triazaphenanthrene 475

J. 2,5,6-Triazaphenanthrene 476

K. 4,5,7-Triazaphenanthrene 477

L. 1,2,3,4-Tetrazaphenanthrene 478

M. 1,4,7,10-Tetrazaphenanthrene 479

N. 2,3,4,6-Tetrazaphenanthrene 480

O. 2,3,5,6-Tetrazaphenanthrene 481

P. 1,3,5,6,8,10-Hexazaphenanthrene 482

References 482

VIII. Azabenzonaphthenes 484
By James H. Richmond

1. Historical 484

2. Nomenclature 485

3. Monoazabenzonaphthenes 485

4. Polyazabenzonaphthenes 517

References 546

IX. The Ultraviolet Absorption Spectra of Polycyclic Heterocyclic Aromatic Compounds 551
By G. M. Badger

1. Aromatic Hydrocarbons and Azahydrocarbons 551

2. The Color of Aromatic Azahydrocarbons 558

3. Absorption Spectra of Diazines and Related Compounds 559

4. The Effect of Substituents 561

References 566

Naphthalimides: Addendum 567
By C. F. H. Allen

Index 571