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Part Ⅰ Isoxazoles and Related Compounds＆By Adolfo Quilico 1

Introduction 1

Nomenclature and Numbering System 3

Chapter Ⅰ．Isoxazoles 5

Ⅰ．Methods of Preparation of Isoxazoles 5

A．Synthesis from 1,3-Dicarbonyl Compounds and Hydroxylamine 6

B．Synthesis from α-Acetylenic Ketones and Aldehydes with Hy-droxylamine 14

C．Synthesis from Halogenated α,β-Ethylenic Aldehydes or Ke-tones and Hydroxylamine 16

D．Isoxazoles from α,β-Unsaturated Ketones and Hydroxylamine 16

E．Synthesis from α,β-Dihaloketones and Hydroxylamine 16

F．Synthesis from Hydroxamyl Chlorides 18

G．Synthesis from Nitrile Oxides 19

H．Synthesis with Fulminic Acid and Acetylenic Derivatives 22

I．Synthesis from Acetylenic Derivatives and Nitrolic Acids 23

J．Synthesis from Primary Nitroparaffins,Nitrostilbenes,and Re-lated Compounds 24

K．Synthesis from Unsaturated Compounds and Nitric(Nitrous)Acid 27

L．Isoxazoles from Isoxazolines 32

M．Other Isoxazole Syntheses 33

N．Isoxazoles from Other Heterocycles 34

Ⅱ．The Chemical Behavior of Isoxazoles 41

A．Basic Properties 41

B．Action of Reducing Agents 42

C．Oxidation 43

D．Action of Alkali,Alkaline Alkoxides,and Other Basic Reagents 44

E．Action of Ammonia,Hydroxylamine,Hydrazine,Aromatic Amines,and Hydrazines 48

F．Action of Halogens 49

G．Action of Chlorosulfonic Acid 49

H．Action of Nitric Acid and Mixed Acids 50

I．Action of Grignard Reagent 50

J．Action of Alkyl Iodides and Sulfates 50

Ⅲ．Isoxazole and Its Alkyl and Aryl Derivatives 53

A．Isoxazole 53

B．Methylisoxazoles 54

C．Homologous Alkyl-and Alkenylisoxazoles 56

D．Phenylisoxazoles 57

E．Homologous Aryl-and Alkylarylisoxazoles 59

F．Isoxazoles Containing Heterocyclic Substituents 62

Ⅳ．Isoxazole Derivatives 66

A．Halogen Derivatives 66

B．Nitro Derivatives 67

C．Sulfonic Acids 70

D．Alcohols,Glycols,and Ethers 71

E．Amines 73

F．Isoxazoles with Other Nitrogen-Containing Functions 75

G．Aldehydes 77

H．Ketones 79

I．Carboxylic Acids 82

J．Amino Acids 88

Chapter Ⅱ．Isoxazolines 95

Ⅰ．Methods of Preparation of Isoxazolines 95

A．From α,β-Unsaturated Ketones and Hydroxylamine 96

B．From β-Chloroketones and Hydroxylamine 99

C．From Ethylenic Derivatives and Nitrile Oxides 99

D．From Isoxazoline N-Oxides 102

E．From Quaternary Salts 102

Ⅱ．The Chemical Behavior of Isoxazolines 102

Ⅲ．Substituted Isoxazolines 104

A．Halo Derivatives 104

B．Hydroxy Derivatives 105

C．Alcohols,Aldehydes,and Ketones 105

D．Carboxylic Acids 105

E．Stereochemistry of 2-Isoxazolines 105

Ⅳ．Isoxazoline N-Oxides 111

A．Methods of Preparation 111

B．Chemical Behavior of Isoxazoline N-Oxides 113

Ⅴ．4,5-Dioxoisoxazolines 115

Chapter Ⅲ．Isoxazolones 117

Ⅰ．Methods of Preparation of 5-Isoxazolones 118

A．Synthesis from β-Ketonic Esters and Hydroxylamine 118

B．Synthesis from α-Acetylenic Esters and Hydroxylamine 119

C．Synthesis from α,β-Unsaturated Esters and Hydroxylaminc 119

D．Synthesis from Sulfur Derivatives of β-Ketonic Esters and Hy-droxylamine 119

E．Synthesis with Hydroxamyl Chlorides and Nitrile Oxides 120

F．Synthesis from β-Ketonic or α-Acetylenic Esters and Aldoximes 121

G．Synthesis from β-Ketonic and α-Acetylenic Nitriles,and Hy-droxylamine 121

H．Other Isoxazolone Syntheses 121

Ⅱ．The Chemical Behavior of 5-Isoxazolones 124

A．Acidic Properties 124

B．Action of Reducing Agents 126

C．Action of Oxidants 126

D．Hydrolytic Cleavage of the Isoxazolone Ring 127

E．Action of Halogens 127

F．Action of Nitrous Acid 128

G．Condensation Reaction with Compounds Containing Carbonyl or Dichloromethyl Groups 128

H．Condensation Reactions with Aromatic Nitroso Bases 129

I．Coupling with Diazonium Salts 129

J．Reactions with Hydrazine Derivatives,Hydroxylamine,and Formamidines 130

K．Action of Grignard Reagents 130

L．Condensation with Ortho Esters 130

Ⅲ．5-Isoxazolones and Their Derivatives 132

A．Alkyl-and Aryl-5-lsoxazolones 132

B．Unsaturated Isoxazolones 132

C．Haloisoxazolones 134

D．5-Iminoisoxazolones 135

E．Isonitrosoisoxazolones 138

F．Nitroisoxazolones 139

G．Isoxazolone Azomethines 139

H．Azo Derivatives 140

I．Alcohols,Aldehydes,Ketones,and Carboxylic Acids of 5-Iso-xazolones 142

J．Arylaminomethyleneisoxazolones 145

Ⅳ．4-Isoxazolones 149

Ⅴ．3-Isoxazolones 151

Chapter Ⅳ．Polynuclear Isoxazole Types 153

Ⅰ．Biisoxazoles 153

A．Synthesis of Biisoxazoles 153

B．Properties and Chemical Behavior of Biisoxazoles 157

Ⅱ．Biisoxazolines 158

Ⅲ．Triisoxazoles and Polyisoxazoles 158

Ⅳ．Benzisoxazoles 159

A．Indoxazenes 160

B．Anthranils 166

Ⅴ．Other Polynuclear Condensed Isoxazoles 173

A．Naphthoisoxazoles 173

B．Anthracene and Anthraquinone Isoxazoles 174

C．Other Polynuclear Types 175

Chapter Ⅴ．The Physico-Chemical Properties of Isoxazole and Its De-rivatives＆By Giovanni Speroni 177

Ⅰ．Isoxazole,Alkyl-and Arylisoxazoles 177

Ⅱ．Isoxazolecarboxylic Acids 198

Ⅲ．Hydroxyisoxazoles and Isoxazoleamines(Isoxazolones and Isoxa-zolonimides) 206

Ⅳ．Benzisoxazoles 213

Chapter Ⅵ．Applications of Isoxazole Derivatives 223

Ⅰ．Isoxazole Derivatives of Pharmacological Significance 223

A．Analeptics 223

B．Sulfa Drugs 225

C．Other Isoxazole Drugs 225

Ⅱ．Other Applications of Isoxazole Derivatives 227

Chapter Ⅶ．Isoxazolidines 229

Ⅰ．Isoxazolidines 229

Ⅱ．Isoxazolidones 230

Part Ⅱ Oxadiazoles and Related Compounds＆By Lyell C．Behr 233

Chapter Ⅷ．1,2,3-Oxadiazoles 235

Ⅰ．The Aliphatic Diazo Compounds 235

Ⅱ．The＂Diazophenols＂ 237

Ⅲ．The Sydnones 240

Chapter Ⅸ．1,2,4-Oxadiazoles 245

Ⅰ．General 245

Ⅱ．Alkyl and Aryl Derivatives 245

Ⅲ．Carboxylic Acids and Their Derivatives 252

Ⅳ．Alcohols 253

Ⅴ．Amino Compounds 253

Ⅵ．Hydroxyl Derivatives 255

Ⅶ．Acetonyl Compounds 257

Ⅷ．Oxadiazolines(Hydrazoximes) 258

Ⅸ．Oxadiazolidines 259

Chapter Ⅹ．1,3,4-Oxadiazoles 263

Ⅰ．General 263

Ⅱ．Aryl-1,3,4-oxadiazoles 263

Ⅲ．Dialkyl-1,3,4-oxadiazoles 264

Ⅳ．Diaryl-and Arylalkyl-l,3,4-oxadiazoles 265

Ⅴ．＂Cyclic Azo Compounds＂ 269

Ⅵ．Amino-l,3,4-oxadiazoles 271

Ⅶ．1,3,4-Oxadiazoles with Sulfur-Containing Substituents 272

Ⅷ．1,3,4-Oxadiazolines 274

Ⅸ．1,3,4-Oxadiazolones 274

Ⅹ．Condensed Systems 277

Ⅺ．Applications of 1,3,4-Oxadiazoles 278

Chapter Ⅺ．Furazans 283

Ⅰ．General 283

Ⅱ．Furazans 284

A．The Dialkylfurazans 284

B．Arylfurazans 285

C．Diaryl-and Arylalkylfurazans 285

D．Hydroxyfurazans 287

E．Furazan Ketones 287

F．Furazancarboxylic Acids 289

G．Aminofurazans 291

H．Condensed Furazans 292

Ⅲ．Furoxans 295

A．Structure 295

B．Monosubstituted Furoxans 298

C．Dialkylfuroxans 298

D．Diaryl-and Arylalkylfuroxans 299

E．Carbonyl Compounds 302

F．Furoxancarboxylic Acids 303

G．Other Substituted Furoxans 305

H．Condensed Fuorxans 305

Ⅳ．Fulminic Acid Derivatives 309

Chapter Ⅻ．Dioxazoles,Dioxadiazoles,and Oxatriazoles 321

Ⅰ．Dioxazoles 321

Ⅱ．Dioxadiazoles 322

Ⅲ．Oxatriazoles 323

Part Ⅲ Oxazines and Related Compounds＆By R．L．McKee 327

Chapter ⅩⅢ．The 1,2-Oxazines 329

Ⅰ．Monocyclic Systems 329

Ⅱ．Condensed 1,2-Oxazine Systems 335

A．Derivatives of 2,3,1H-Benzoxazine 335

B．Derivatives of 1,2,4H-Benzoxazine 338

C．Derivatives of Naphth[1,8-de][1,2]oxazine 338

D．Derivatives of 3H-Phenanthr[9,10-d][1,2]oxazine 339

E．Furazano[3,4-d][1,2]oxazine 339

Chapter ⅩⅣ．The 1,3-Oxazines 341

Ⅰ．Monocyclic Systems 341

Ⅱ．Condensed Systems 350

A．1,3-Benzoxazines 351

B．3,1-Benzoxazines 359

C．Pyrido[1,2-b][1,3]oxazine 366

D．2-Naphth[2,3-e][1,3]oxazine 366

E．4-Naphth[2,3-d][1,3]oxazine 366

F．2-Naphth[2,1-e][1,3]oxazine and 1-Naphth[1,2-e][1,3]oxazine 366

G．4-Naphth[1,2-d][1,3]oxazine 366

H．1-Naphth[2,1-d][1,3]oxazine 366

I．Naphth[1,8][1,3]oxazine 367

J．4H-Anthr[1,2-d][1,3]oxazine 367

K．Naphthaceno[5,6-de][1,3]oxazine 367

L．2-Pyrido[3,2-h][1,3]benzoxazine 367

M．4-Pyrido[2,3-h][3,1]benzoxazine 367

N．Thianaphthenooxazines 368

O．5-Isoindolo[2．1-a][3,1]berzoxazine 368

P．Pyrazolobenzoxazines 368

Q．Pyrazolo[4,3-e][1,3]oxazine 369

R．Isoxazolo[4,5-e][1,3]oxazine 369

S．Indazolylbenzoic Acid 369

T．Indolo[3,2-d][1,3]oxazine or Indolo[2,3-d][1,3]oxazinc 370

U．3,4-[Indolo(1,2)]-5,6[indolo(3,2)]-△5-dihydro-1,3-oxazine 370

V．4H,5H-Pyrano[3,4-e][1,3]oxazine 370

W．1,3-Oxazino[2,3-e]pyrazole 371

Chapter ⅩⅤ．The 1,4-Oxazlnes 377

Ⅰ．Monocyclic Systems 377

Ⅱ．Condensed Systems 394

A．1,4-Benzoxazines 394

B．5,8-Methano-1,4-benzoxazine 397

C．8-Oxa-3-azabicyclo[3,2,1]octane 397

D．3-Oxa-8-azabicyclo[3,2,1]octane(Morphopyrrolidine)and 3-Oxa-9-azabicyclo[3,3,1]nonane(Morphopiperidine) 398

E．Cyclopenta[b][1,4]benzoxzzine 398

F．4H-Naphth[2,3][1,4]oxazine 398

G．1H-Naphth[2,1][1,4]oxazine 399

H．2H-Naphth[1,2][1,4]oxazine 399

I．1H-Anthr[2,1][1,4]oxazine 400

J．12H-Acenaphtho[1,2-b][1,4]benzoxazine 400

K．3-Methyl-6,8-dioxa-3-azabicyclo[3,2,1]octane 400

L．3-Oxa-6-thi-8-azabicyclo[3,2,1]octane 400

M．Thiazolooxazines 401

N．1H-Pyrrolo[2,1-c][1,4]oxazine 401

O．Pyrrolo[3,4-b][1,4]oxazine 401

P．Pyrazolo[3,4-b][1,4]oxazine 401

Q．5H-[1,4]-Oxazino[2,3-d]pyrimidine 402

R．Triazolobenzoxazine 402

S．Imidazo[b][1,4]benzoxazine 402

T．Imidazo[f][1,4]benzoxazine 402

U．5H-Pyrido[1,2,3-de][l,4]benzoxazine 403

V．Pyrido[3,2-b][1,4]benzoxazine,Pyrido[4,3-b][1,4]benzoxazinc and Pyrido[3,4-b][1,4]benzoxazine 403

W．2H-[1,4]-Oxazino[b]phenazine 403

X．7H-[1,4]-Oxazino[de]phenazine 403

Y．[1,4]Benzoxazino[3,2-b][1,4]benzoxazine(Diphendioxazine) 404

Z．11H-Quinoxalo[2,3-b][1,4]benzoxazine(Diphenazineoxazine) 404

A′．5H-6-Oxa-12,14-dithia-5,7,13-triazapentacene(Dibenzothi-azoxine) 404

B′．1H-[1,4]-Oxazino[4,3-a]indole 404

C′．Pyrimidino[4,5-b][1,4]benzoxazine 405

Ⅲ．Condensed Systems-Phenoxazines and Allied Compounds 407

A．Phenoxazines 408

B．Phenoxazones,Phenoxazines,and their Salts:the Phenoxa-zonium and Phenazoxonium Compounds 414

C．Triphendioxazine and Related Compounds 432

D．Trinaphthodioxazine 434

E．Quinoxalo[2,3-b]phenoxazines,triphenazineoxazincs 434

F．7H-Benzo[a][1,4]benzoxazino[3,2-i]phenazine 435

G．Pyrido[3,2-a]phenazoxonium Salts 435

H．Chrysophenoxazine 435

Chapter ⅩⅥ．Systems of Two Oxygen Atoms and One Nitrogen Atom:the Dioxazines 443

Ⅰ．Monocyclic Systems 443

Ⅱ．Condensed Systems 444

Chapter ⅩⅦ．Systems of Three Oxygen Atoms and One Nitrogen Atom 445

Ⅰ．Monocyclic Systems 445

Ⅱ．Condensed Systems 445

Chapter ⅩⅧ．Systems of One Oxygen Atom and Two Nitrogen Atoms:the Oxadiazines 447

Ⅰ．Monocyclic Systems 447

A．1,2,4,4H-and 1,2,4,6H-Oxadiazines 447

B．1,2,5-Oxadiazines 448

C．1,2,6-Oxadiazines 449

D．1,3,4-Oxadiazines 450

E．1,3,5-Oxadiazines 452

Ⅱ．Condensed Systems 454

A．The Benzoxadiazines 454

B．1H-Anthr[2,3][1,3,4]oxadiazine 456

C．2H-Phenanthr[9,10][1,3,4]oxadiazine 456

D．8H-Acenaphth[1,2][1,3,4]oxadiazine 456

E．1,3,4-Oxadiazino[6,5-b]indole 456

F．Benzopyrano-oxadiazines 457

G．Anhydride of 7,9-Bis-hydroxymethyleneuric Acid 457

H．5H-Pyrazolo[3,2-c][2,1,4]benzoxadiazine 457

I．Pyrid[1,2-c][1,3,5]oxadiazine 458

Chapter ⅩⅨ．Systems of One Oxygen Atom and Three Nitrogen Atoms 459

Ⅰ．Monocyclic Systems 459

Ⅱ．Condensed Systems 460

Chapter ⅩⅩ．Systems of Two Oxygen Atoms and Two Nitrogen Atoms 461

Ⅰ．Monocyclic Systems 461

Ⅱ．Condensed Systems 461

Chapter ⅩⅪ．Systems of More Than Four Hetero Atoms,Nitrogen and Oxygen 463

Subject Index 467