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Applied Organic Chemistry. Reaction Mechanisms and Experimental Procedures in Medicinal Chemistry. Edition No. 1

  • ID: 5179030
  • Book
  • December 2020
  • 856 Pages
  • John Wiley and Sons Ltd
An indispensable guide for all synthetic chemists who want to learn about the most relevant reactions and reagents employed to synthesize important heterocycles and drugs!

The synthesis of natural products, bioactive compounds, pharmaceuticals, and drugs is of fundamental interest in modern organic chemistry. New reagents and reaction methods towards these molecules are being constantly developed. By understanding the mechanisms involved and scope and limitations of each reaction applied, organic chemists can further improve existing reaction protocols and develop novel efficient synthetic routes towards frequently used drugs, such as Aspirin or Penicillin.

Applied Organic Chemistry provides a summary of important (name) reactions and reagents applied in modern organic chemistry and drug synthesis. It covers rearrangement, condensation, olefination, metathesis, aromatic electrophilic substitutions, Pd-catalyzed C-C bond forming reactions, multi-component reactions, as well as oxidations and reductions. Each chapter is clearly structured, providing valuable information on reaction details, step-by-step mechanism, experimental procedures, applications, and (patent) references. By providing mechanistic information and representative experimental procedures, this book is an indispensable guide for researchers and professionals in organic chemistry, natural product synthesis, pharmaceutical, and medicinal chemistry, as well as post-graduates preparing themselves for a job in the pharmaceutical industry. - Hot Topic: Reviews important classes of organic reactions (incl. name reactions) and reagents in medicinal chemistry. - Useful: Provides information on reaction details, common reagents, and functional group transformations used to synthesize natural products, bioactive compounds, drugs, and pharmaceuticals, e.g. Aspirin, Penicillin. - Unique: For every reaction the mechanism is explained step by step, and representative experimental procedures are given, unlike most books in this area. - User-friendly: Chapters are clearly structured making it easy for the reader to compare different reactions.

Applied Organic Chemistry is an indispensable guide for researchers and professionals in organic chemistry, natural product synthesis, pharmaceutical, and medicinal chemistry, as well as post-graduates preparing themselves for a job in the pharmaceutical industry.
Note: Product cover images may vary from those shown

Volume 1

Preface xxiii

About the Author xxv

About the Book xxvii

Acknowledgments xxix

List of Abbreviations xxxi

1 Rearrangement Reactions 1

Baeyer–Villiger Oxidation or Rearrangement 1

Mechanism 2

Application 2

Experimental Procedure (from patent US 5142093A) 3

Dakin Oxidation (Reaction) 3

Mechanism 4

Application 4

Experimental Procedure (from patent EP0591799B) 4

Bamberger Rearrangement 5

Mechanism 5

Experimental Procedure (from patent CN102001954B) 6

Beckmann Rearrangement 6

Mechanism 6

Application 7

Experimental Procedure (general) 7

Preparation of Caprolactam (from patent US 3437655A) 7

Benzilic Acid Rearrangement 8

Mechanism 9

Application 9

Experimental Procedure (from patent US20100249451B) 9

Baker–Venkataraman Rearrangement 9

Mechanism 10

Application 10

Experimental Procedure (from patent CN105985306B) 10

Claisen Rearrangement 11

Mechanism 11

Application 12

Experimental Procedure (from patent WO2016004632A1) 13

Eschenmoser–Claisen Rearrangement 13

Mechanism 13

Ireland–Claisen Rearrangement 14

Mechanism 14

Johnson–Claisen Rearrangement 15

Mechanism 15

Overman Rearrangement 15

Mechanism 16

Cope Rearrangement 16

Mechanism 17

Application 17

Experimental Procedure (from patent US 4421934A) 17

Curtius Rearrangement 17

Mechanism 18

Application 18

Experimental Procedure (from patent EP2787002A1) 19

Demjanov Rearrangement 19

Mechanism 20

Application 21

Experimental Procedure (from Reference [14], copyright 2008, American Chemical Society) 21

Tiffeneau–Demjanov Rearrangement 22

Mechanism 22

Application 23

Experimental Procedure (from Reference [10], copyright,The Royal Society of Chemistry) 23

Fries Rearrangement 23

Mechanism 24

Application 24

Experimental Procedure (from patent US9440940B2) 25

Favorskii Rearrangement 25

Mechanism 25

Application 26

Experimental Procedure (from patent EP3248959A2) 26

Fischer–Hepp Rearrangement 26

Mechanism 27

Experimental Procedure (general) 27

Hofmann Rearrangement (Hofmann degradation of amide) 28

Mechanism 28

Application 29

Experimental Procedure (from patent CN105153023B) 29

Hofmann–Martius Rearrangement 29

Mechanism 30

Experimental Procedure (from patent DD295338A5) 30

Lossen Rearrangement 31

Mechanism 31

Application 32

Experimental Procedure (from patent EP2615082B1) 32

Orton Rearrangement 32

Mechanism 33

Pinacol–Pinacolone Rearrangement 33

Mechanism 34

Application 34

Experimental Procedure (general) 34

Rupe Rearrangement/Meyer–Schuster Rearrangement 34

Rupe Rearrangement 35

Meyer–Schuster Rearrangement 35

Mechanism 35

Application 36

Experimental Procedure (from patent US4088681A) 36

Schmidt Rearrangement or Schmidt Reaction 36

Mechanism 37

Application 37

Experimental Procedure (from patent WO2009026444A1) 38

Wagner–Meerwein Rearrangement 38

Mechanism 38

Application 39

Wolff Rearrangement 39

Mechanism 39

Alternatively 40

Application 40

Experimental Procedure (from patent US9175041B2) 9175041B2 40

Arndt–Eistert Homologation or Synthesis 41

Mechanism 41

Application 42

Experimental Procedure (from patent US9399645B2) 42

Step 1 42

Step 2 42

Zinin Rearrangement or Benzidine and Semidine Rearrangements 42

Mechanism 43

Experimental Procedure (from patent US20090069602A1) 44

References 45

Baeyer-Villiger Oxidation or Rearrangement 45

Dakin Oxidation or Reaction 47

Bamberger Rearrangement 48

Beckmann Rearrangement 48

Benzilic Acid Rearrangement 50

Baker–Venkataraman Rearrangement 51

Claisen Rearrangement/Eschenmoser–Claisen Rearrangement/Ireland–Claisen Rearrangement/Johnson–Claisen Rearrangement/Overman Rearrangement 52

Cope Rearrangement 53

Curtius Rearrangement 54

Demjanov Rearrangement 56

Tiffeneau–Demjanov Rearrangement 56

Fries Rearrangement 56

Favorskii Rearrangement 58

Fischer–Hepp Rearrangement 58

Hofmann Rearrangement (Hofmann Degradation of Amide) 59

Hofmann–Martius Rearrangement 60

Lossen Rearrangement 60

Orton Rearrangement 61

Pinacol–Pinacolone Rearrangement 62

Rupe Rearrangement/Meyer–Schuster Rearrangement 62

Schmidt Rearrangement or Schmidt Reaction 63

Wagner–Meerwein Rearrangement 64

Wolff Rearrangement 65

Arndt–Eistert Homologation or Synthesis 66

Zinin Rearrangement or Benzidine and Semidine Rearrangements 67

2 Condensation Reaction 69

Aldol Condensation Reaction 69

Application 70

Experimental Procedure (general) 71

Enantioselective Aldol Reaction (from patent US 6919456B2) 71

Mukaiyama Aldol Reaction 72

Mechanism 72

Application 72

Experimental Procedure (from patent DE102013011081A1) 73

Evans Aldol Reaction 73

Mechanism 74

Application 74

Experimental Procedure (from patent WO2013151161A1) 74

Henry Reaction 75

Mechanism 75

Application 76

Experimental Procedure (from patent US 6919456B2) 76

Preparation of Chiral Catalyst 76

Nitro-Aldol Reaction 76

Benzoin Condensation 76

Mechanism 77

Application 77

Experimental Procedure (from patent DE3019500C2) 78

Claisen Condensation 78

Mechanism 78

Application 79

Experimental Procedure (from patent US9884836B2) 79

Darzens Glycidic Ester Condensation 80

Mechanism 80

Application 81

Experimental Procedure (from patent JP2009512630A) 81

Dieckmann Condensation 81

Mechanism 82

Application 82

Experimental Procedure (from patent US 7132564 B2) 82

Knoevenagel Condensation 83

Mechanism 83

Application 84

Lumefantrine 84

Experimental Procedure (from patent WO2010136360A2) 84

Pechmann Condensation (synthesis of coumarin) (also called von Pechmann condensation) 85

Mechanism 85

Application 86

Experimental Procedure (from patent US7202272B2) 86

Perkin Condensation or Reaction 86

Mechanism 87

Application 88

Experimental Procedure (from patent US4933001A) 88

Stobbe Condensation 88

Mechanism 89

Application 89

Experimental Procedure (from patent US20160137682A1) 90

References 90

Aldol Condensation Reaction 90

Mukaiyama Aldol Reaction 93

Evans Aldol Reaction 96

Henry Reaction 98

Benzoin Condensation 99

Claisen Condensation 101

Darzens Glycidic Ester Condensation 102

Dieckmann Condensation 103

Knoevenagel Condensation 105

Pechmann Condensation 106

Perkin Condensation or Reaction 107

Stobbe Condensation 108

3 Olefination, Metathesis, and Epoxidation Reactions 111

Olefination 111

Corey–Winter Olefin Synthesis 111

Mechanism 112

Application 112

Experimental Procedure (from patent US5807866A) 112

Horner–Wadsworth–Emmons Reaction 113

Mechanism 113

Application 113

Experimental Procedure (from patent JPWO2015046403A1) 114

Julia–Lythgoe Olefination 114

Mechanism 115

Modified Julia Olefination 115

Mechanism 115

Application 116

Experimental Procedure (from patent CN103313983A) 116

Julia–Kocienski Olefination 117

Application 117

Experimental Procedure (from patent WO2016125086A1) 118

Kauffmann Olefination 118

Mechanism 119

Application 119

Experimental Procedure (from patent WO2014183211A1) 119

Peterson Olefination 119

Mechanism 120

Application 121

Experimental Procedure (from patent WO2017149091A1) 121

Petasis Olefination 122

Mechanism 122

Application 123

Experimental Procedure (from patent US5087790A) 123

Tebbe Olefination 123

Mechanism 123

Application 124

Experimental Procedure (from patent US8809558B1) 124

Wittig Reaction or Olefination 124

Mechanism 125

Application 126

Experimental Procedure (from patent WO2006045010A2) 126

Metathesis 127

Olefin Metathesis 127

Ring-Closing Metathesis 127

Mechanism 128

Experimental Procedure (from patent US20022018351A1) 128

Cross Metathesis 128

Ring-Opening Metathesis 128

Ring-Opening Metathesis Polymerization (ROMP) 129

Asymmetric Epoxidation 129

Sharpless Asymmetric Epoxidation 129

Mechanism 129

Application 130

Experimental Procedure (from patent DE102014107132A1) (For more experimental procedures see Chapter 15) 130

Jacobsen–Katsuki Asymmetric Epoxidation 130

Mechanism 131

Application 131

Experimental Procedure (from patent US7501535B2) 132

Shi Asymmetric Epoxidation 132

Mechanism 133

Application 133

Experimental Procedure (from patent EP1770095A1) 133

Sharpless Asymmetric Dihydroxylation 134

Mechanism 135

Application 135

Experimental Procedure (from patent US7472570B1) 136

Sharpless Asymmetric Aminohydroxylation 136

Mechanism 137

Application 137

Experimental Procedure (from patent US8987504B2) 137

Woodward cis-Dihydroxylation 138

Mechanism 138

Application 139

Experimental Procedure (from patent WO1997013780A1) 139

Prévost trans-Dihydroxylation Reaction 140

Mechanism 140

Application 141

References 141

Corey–Winter Olefin Synthesis 141

Horner–Wadsworth–Emmons Reaction 141

Julia–Lythgoe Olefination 143

Julia–Kocienski Olefination 144

Kauffmann Olefination 146

Peterson Olefination 146

Petasis Olefination 148

Tebbe Olefination 148

Wittig Reaction or Olefination 149

Metathesis 150

Sharpless Asymmetric Epoxidation 150

Jacobsen–Katsuki Asymmetric Epoxidation 152

Shi Asymmetric Epoxidation 153

Sharpless Asymmetric Dihydroxylation 155

Sharpless Asymmetric Aminohydroxylation 156

Woodward cis-Dihydroxylation 158

Prévost trans-Dihydroxylation Reaction 158

4 Miscellaneous Reactions 161

Alder-Ene Reaction 161

Mechanism 161

Application 162

Experimental Procedure (from patent WO2015149068A1) 162

Appel Reaction 162

Mechanism 163

Application 163

Experimental Procedure (from patent WO2015134973A1) 163

Barton Decarboxylation 164

Mechanism 164

Application 165

Experimental Procedure (from patent US6080563A) 165

Barton Nitrite Photolysis (Barton nitrite ester reaction) 166

Mechanism 166

Application 167

Experimental Procedure (from patent US3214427A) 167

Brown Hydroboration 167

Mechanism 168

Application 168

Experimental Procedure (from patent WO1995013284A1) 168

Bucherer Reaction 169

Mechanism 169

Application 170

Experimental Procedure (from Reference [7], copyright 2020, American Chemical Society) 170

Chichibabin Reaction 170

Mechanism 171

Application 171

Experimental Procedure Amination of 3-Picoline (from patent EP0098684B1) 171

Chugaev Elimination Reaction 172

Mechanism 173

Application 173

Experimental Procedure (from Reference [10], copyright 2008, American Chemical Society) 173

Cannizzaro Reaction 173

Mechanism 174

Application 175

Experimental Procedure (general) 175

Cope Elimination Reaction 175

Mechanism 175

Application 176

Experimental Procedure (from Reference [3], copyright, Organic Syntheses) 176

Corey–Fuchs Reaction 176

Mechanism 177

Application 177

Experimental Procedure (from patent JP2015500210A) 178

Formation of Compound B 178

Formation of Compound C 178

Corey–Nicolaou Macrolactonization 178

Mechanism 179

Application 179

Experimental Procedure (patent US20060004107A1) 179

Danheiser Annulation 180

Mechanism 181

Danheiser Benzannulation 181

Mechanism 182

Application 182

Experimental Procedure (from Reference [22], Copyright 2013, American Chemical Society) 182

Diels–Alder Reaction 183

Normal Electron Demand Diels–Alder Reaction 183

Inverse electron Demand Diels–Alder Reaction 183

Hetero–Diels–Alder Reaction 183

Mechanism 184

Application 184

Experimental Procedure (from patent CA 2361682A1) 184

Dutt–Wormall Reaction 185

Mechanism 185

Étard Reaction 185

Mechanism 186

Application 186

Experimental Procedure (US8957255B2) 186

Finkelstein Reaction 187

Mechanism 187

Application 188

Experimental Procedure (from patent WO2019134765A1) 188

Fischer–Speier Esterification 188

Mechanism 188

Experimental Procedure (general) 189

Mukaiyama Esterification 189

Mechanism 190

Application 190

Experimental Procedure (from patent US4206310A) 190

Yamaguchi Esterification 191

Mechanism 191

Application 192

Experimental Procedure (from patent WO 2019033219A1) 192

Grignard Reaction 193

Mechanism 193

Application 194

Experimental Procedure (general) 194

Experimental Procedure (from patent WO1994028886A1) 195

Gabriel Synthesis 195

Mechanism 196

Application 196

Experimental Procedure (from patent US9540358B2) 197

Hell–Volhard–Zelinsky Reaction 197

Mechanism 198

Application 198

Experimental Procedure (from patent WO199101199A1) 199

Hofmann Elimination or Exhaustive Methylation 199

Mechanism 199

Application 200

Hosomi–Sakurai Reaction 200

Mechanism 201

Application 201

Experimental Procedure (from patent WO2019093776A1) 201

Huisgen Cycloaddition Reaction 202

Click Chemistry 202

Mechanism 203

Experimental Procedure (from patent WO2008124703A2) 203

Hunsdiecker Reaction 203

Mechanism 204

Application 204

Experimental Procedure (from patent WO2017060906A1) 204

Keck Asymmetric Allylation 204

Mechanism 205

Application 205

Experimental Procedure (from patent US6603023B2) 205

Thionation Reaction (Lawesson’s Reagent) 206

Mechanism 207

Application 207

Experimental Procedure (general) 207

Michael Addition or Reaction 208

Mechanism 208

Application 209

Experimental Procedure (Aza-Michael Addition) (from patent CN102348693B) 209

Mitsunobu Reaction 209

Mechanism 210

Application 211

Experimental Procedure (from patent US20170145017A1) 211

Morita–Baylis–Hillman Reaction (Baylis–Hillman Reaction) 211

Mechanism 212

Application 213

Experimental Procedure (from patent US20060094739A1) 213

Nozaki–Hiyama–Kishi Reaction 213

Mechanism 214

Application 214

Experimental Procedure (from patent US20190337964A1) 214

Paterno–Büchi Reaction 215

Mechanism 215

Application 215

Experimental Procedure (from Reference [29], copyright 2019, American Chemical Society) 216

Pauson–Khand Reaction 216

Mechanism 217

Application 217

Experimental Procedure (from patent WO2003080552A2) 217

Reformatsky Reaction 218

Mechanism 218

Application 219

Experimental Procedure (from patent US6924386B2) 219

Ritter Reaction 220

Mechanism 220

Application 221

Experimental Procedure (from patent WO1996036629A1) 221

Robinson Annulation 221

Mechanism 222

Application 222

Experimental Procedure (from patent WO2018226102A1) 223

Sandmeyer Reaction 223

Mechanism 224

Application 224

Experimental Procedure (from patent WO20100234652A1) 224

Schotten–Baumann Reaction 225

Mechanism 225

Amide Formation 225

Ester Formation 225

Application 226

Simmons–Smith Reaction 226

Mechanism 227

Application 227

Experimental Procedure (from patent US7019172B2) 228

Stork Enamine Synthesis 228

Mechanism 229

Application 230

Experimental Procedure (from patent US2773099A) 230

Tishchenko Reaction 230

Mechanism 231

Application 231

Experimental Procedure (from Reference [38], copyright 2012, American Chemical Society) 231

Ullmann Coupling or Biaryl Synthesis 232

Mechanism 232

Application 233

Ullmann Biaryl Ether and Biaryl Amine Synthesis/Ullman Condensation 233

Ullmann Biaryl Ether Synthesis 233

Goldberg Reaction (biaryl amines) 233

Ullmann-Type Reaction/Ullmann Condensation 234

Mechanism 234

Application 234

Experimental Procedure (from Patent WO1999018057A1) 234

Weinreb Ketone Synthesis 235

Mechanism 236

Application 237

Experimental Procedure (from patent US9399645B2) 237

Step 1 237

Step 2 237

Williamson Ether Synthesis 238

Mechanism 238

Application 238

Experimental Procedure (from patent WO1994028886A1) 239

Wurtz Coupling or Reaction 239

Mechanism 239

Application 240

Wurtz–Fittig Reaction 240

Mechanism 240

References 240

Alder-Ene Reaction 240

Appel Reaction 242

Barton Decarboxylation 242

Barton Nitrite Photolysis (Barton Nitrite Ester Reaction) 244

Brown Hydroboration 244

Bucherer Reaction 246

Chichibabin Reaction 246

Chugaev Elimination Reaction 247

Cannizzaro Reaction 247

Cope Elimination Reaction 249

Corey–Fuchs Reaction 250

Corey–Nicolaou Macrolactonization 250

Danheiser Annulation/Danheiser Benzannulation 251

Diels–Alder Reaction 252

Dutt–Wormall Reaction 253

Étard Reaction 253

Finkelstein Reaction 254

Fischer–Speier Esterification 255

Mukaiyama Esterification 255

Yamaguchi Esterification 256

Grignard Reaction 257

Gabriel Synthesis 258

Hell–Volhard–Zelinsky Reaction 259

Hofmann Elimination or Exhaustive Methylation 259

Hosomi–Sakurai Reaction 260

Huisgen Cycloaddition Reaction/Click Chemistry 262

Hunsdiecker Reaction 262

Keck Asymmetric Allylation 263

Thionation Reaction (Lawesson’s Reagent) 264

Michael Addition or Reaction 265

Mitsunobu Reaction 266

Morita–Baylis–Hillman Reaction (Baylis–Hillman Reaction) 268

Nozaki–Hiyama–Kishi Reaction 270

Paterno–Büchi Reaction 271

Pauson–Khand Reaction 272

Reformatsky Reaction 274

Ritter Reaction 276

Robinson Annulation 277

Sandmeyer Reaction 279

Schotten–Baumann Reaction 280

Simmons–Smith Reaction 281

Stork Enamine Synthesis 282

Tishchenko Reaction 283

Ullmann Coupling or Biaryl Synthesis 285

Ullmann Biaryl Ether and Biaryl Amine Synthesis/Ullman Condensation 286

Weinreb Ketone Synthesis 287

Williamson Ether Synthesis 289

Wurtz Coupling or Reaction 290

Wurtz–Fittig Reaction 290

5 Aromatic Electrophilic Substitution Reactions 293

Bardhan–Sengupta Synthesis 293

Mechanism 293

Bogert–Cook Reaction or Synthesis of Phenanthrene 294

Mechanism 294

Friedel–Crafts Reaction 295

Friedel–Crafts acylation 295

Friedel–Crafts alkylation 295

Mechanism 296

Mechanism for Friedel–Crafts Alkylation 297

Application 297

Experimental Procedure (from patent US4814508A) 298

Gattermann Aldehyde Synthesis 298

Mechanism 299

Experimental Procedure (from patent US2067237A) 299

Gattermann–Koch Aldehyde Synthesis 300

Mechanism 300

Experimental Procedure (from patent WO2002020447A1) 301

Haworth Reaction 301

Mechanism 303

Experimental Procedure (from patent CN106977377A) 304

Houben–Hoesch Reaction 304

Mechanism 305

Application 306

Experimental Procedure (from patent EP0431871A2) 306

Kolbe–Schmitt Reaction 306

Mechanism 307

Application 307

Experimental Procedure (from patent US7582787B2) 307

Reimer–Tiemann Reaction 308

Mechanism 308

Application 310

Experimental Procedure (from patent US4324922A) 310

Vilsmeier–Haack Reaction 311

Mechanism 312

Application 313

Experimental Procedure (from patent US5599966A) 313

References 313

Bardhan–Sengupta Synthesis 313

Bogert–Cook Reaction or Synthesis of Phenanthrene 314

Friedel–Crafts Reaction 314

Gattermann Aldehyde Synthesis 317

Gattermann–Koch Aldehyde Synthesis 317

Haworth Reaction 318

Houben–Hoesch Reaction 318

Kolbe–Schmitt Reaction 319

Reimer–Tiemann Reaction 319

Vilsmeier–Haack Reaction 320

6 Pd-Catalyzed C - C Bond-Forming Reactions 323

Suzuki Coupling Reaction 323

Mechanism 324

Application 325

Experimental Procedure (General) 325

Heck Coupling Reaction (Mizoroki–Heck Reaction) 325

Mechanism 326

Application 327

Experimental Procedure (from patent WO2008138938A2) 327

Negishi Coupling Reaction 328

Mechanism 328

Application 329

Experimental Procedure (from patent WO2010026121) 329

Stille Coupling Reaction (Migita–Kosugi–Stille Coupling Reaction) 330

Mechanism 330

Application 330

Experimental Procedure (from patent WO2008012440A2) 331

Sonogashira Coupling Reaction 331

Mechanism 332

Application 332

Experimental Procedure (General) 333

Kumada Cross-Coupling 333

Mechanism 334

Application 335

Experimental Procedure (from patent WO2015144799) 335

Hiyama Coupling Reaction 335

Mechanism 336

Application 336

Experimental Procedure (from patent US20022018351A1) 336

Liebeskind–Srogl Coupling Reaction 337

Mechanism 337

Application 338

Experimental Procedure (from patent WO2008030840A2) 338

Fukuyama Coupling Reaction 338

Mechanism 339

Application 339

Experimental Procedure (from patent US20150336915A1) 339

Buchwald–Hartwig Coupling Reaction (Buchwald–Hartwig Amination) 340

Mechanism 340

Buchwald–Hartwig Amination 340

Application 341

Experimental Procedure (from patent US7442800B2) 341

Tsuji–Trost Allylation 341

Mechanism 342

Application 343

Experimental Procedure (from patent US20190270700A1) 343

References 343

Suzuki Coupling Reaction 343

Heck Coupling Reaction (Mizoroki–Heck Reaction) 345

Negishi Coupling Reaction 347

Stille Coupling Reaction (Migita–Kosugi–Stille Coupling Reaction) 349

Sonogashira Coupling Reaction 351

Kumada Cross-Coupling 353

Hiyama Coupling Reaction 355

Liebeskind–Srogl Coupling Reaction 356

Fukuyama Coupling Reaction 357

Buchwald–Hartwig Coupling Reaction (Buchwald–Hartwig Amination) 358

Tsuji–Trost Allylation 360

7 Multicomponent Reaction 363

Biginelli Reaction (3-Component Reaction [3-CR]) 363

One of Plausible Mechanisms 364

Application 364

Experimental Procedure (from patent US810606062B1) 364

Gewald Reaction (3-Component Reaction [3-CR]) 365

Mechanism 365

Application 366

Experimental Procedure (from patent US20100081823A1) 366

Hantzsch Pyridine Synthesis 366

Mechanism 367

Application 368

Experimental Procedure (from patent US8106062B1) 368

Mannich Reaction 369

Mechanism 369

Application 370

Experimental Procedure (from patent WO2007011910A2) 370

Passerini Reaction (3-Component Reaction [3-CR]) 370

Mechanisms 371

Ionic Mechanism 371

Concerted Mechanism 372

Lactone Formation [3] 372

Application 372

Experimental Procedure (from patent WO1995002566A1) 373

Strecker Amino Acid Synthesis 373

Mechanism 374

Part 1: Formation of α-Aminonitrile 374

Part 2: Hydrolysis of the Nitrile 374

Application 375

Experimental Procedure (from patent US5169973A) 375

Ugi Reaction (4-Component Reaction [4-CR]) 375

Plausible ReactionMechanism 376

Application 377

Experimental Procedure (from patent US20150087600A1) 377

Asinger Reaction (4-Component Reaction [A-4CR]) 378

Application 378

References 379

Biginelli Reaction 379

Gewald Reaction 380

Hantzsch Pyridine Synthesis 381

Mannich Reaction 382

Passerini Reaction 384

Strecker Amino Acid Synthesis 385

Ugi Reaction 386

Asinger Reaction 388

Volume 2

Preface xxi

About the Author xxiii

About the Book xxv

Acknowledgments xxvii

List of Abbreviations xxix

8 Oxidations and Reductions 389

9 Nomenclature and Application of Heterocyclic Compounds 449

10 Synthesis of Some Heterocyclic Compounds Using Named Reactions 469

11 Protection and Deprotection of Common Functional Groups 507

12 Amino Acids and Peptides 519

13 Functional Group Transformation 543

14 Synthesis of Some Drug Molecules 565

15 Common Laboratory Methods 573

16 Common Reagents in Organic Synthesis 603

Appendix A List of Medicines (Partial) and Nutrients 671

Index 737

Note: Product cover images may vary from those shown
Surya K. De
Note: Product cover images may vary from those shown