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Heterocyclic Chemistry in Drug Discovery,9781118148907
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Heterocyclic Chemistry in Drug Discovery

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Edition:
1st
ISBN13:

9781118148907

ISBN10:
1118148908
Format:
Hardcover
Pub. Date:
4/15/2013
Publisher(s):
Wiley
List Price: $160.00

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Summary

Providing a handy reference to synthetic methods and practical techniques, Heterocyclic Chemistry in Drug Discovery fuses heterocyclic chemistry and drug discovery, two areas that have gone hand-in-hand in the practice of medicinal chemistry, but have not yet come together for training novice medicinal chemists and students. Rich with numerous case studies to illustrate the real-world drug discovery applications, this book brings together the collective 100-plus years of drug discovery experience from academic and industry contributors to provide valuable insight into the role and application of heterocyclic chemistry for pharmaceuticals.

Author Biography

JIE JACK LI, PhD, is a chemist at Bristol-Myers Squibb Company. He has authored or edited several books published by Wiley, including Name Reactions in Heterocyclic Chemistry, Name Reactions for Functional Group Transformations, Name Reactions for Homologations (Part I and Part ll ), Name Reactions for Carbocyclic Ring Formations, Contemporary Drug Synthesis, The Art of Drug Synthesis, and Modern Drug Synthesis.

Table of Contents

Chapter 1 Introduction 1

1.1 Nomenclature of Heterocycles 1

1.2 Aromatic Heterocycles 4

1.3 Importance of Heterocycles in Life 5

1.4 Importance of Heterocycles in Drug Discovery 8

PART I FIVE-MEMBERED HETEROCYCLES WITH ONE HETEROATOM 17

Chapter 2 Pyrroles 18

2.1 Introduction 18

2.2 Reactivity 22

2.3 Construction of the Pyrrole Rings 34

2.4 Palladium Chemistry of Pyrroles 44

2.5 Possible Liabilities of Pyrrole-Containing Drugs 46

2.6 Problems 49

2.7 References 51

Chapter 3 Indoles 54

3.1 Introduction 54

3.2 Reactivity of the Indole Ring 58

3.3 Construction of the Indole Rings 64

3.4 Oxindole-Containing Drug Synthesis 88

3.5 Cross-coupling Reactions for Indoles 91

3.6 Azaindole 104

3.7 Possible Liabilities of Drugs Containing 3-Methylindole 109

3.8 Problems 111

3.9 References 113

Chapter 4 Furans, Benzofurans, Thiophenes, and Benzothiophenes 119

4.1 Introduction 119

4.2 Furans and Benzofuran 126

4.3 Thiophenes and Benzothiophenes 158

4.4 Possible Liabilities of Furan and Thiophene-Containing Drugs 185

4.5 Problems 187

4.6 References 191

PART II FIVE-MEMBERED HETEROCYCLES WITH TWO OR MORE HETEROATOMS 197

Chapter 5 Pyrazoles, Pyrazolones, and Indazoles 198

5.1 Introduction 198 viii

5.2 Reactivity of the Pyrazoles and Indazoles 202

5.3 Construction of the Pyrazole and Indazole Rings 206

5.4 Pyrazolone-containing Drugs 217

5.5 Indazole-containing Drugs 220

5.6 Problems 223

5.7 References 226

Chapter 6 Oxazoles, Benzoxazoles, and Isoxazoles 231

6.1 Introduction 231

6.2 Construction of the Heterocyclic Ring 235

6.3 Reactivity 244

6.4 Cross-Coupling Reactions 250

6.5 Selected Reactions of Isoxazoles 269

6.6 Possible Liabilities of Oxazole-Containing Drugs 270

6.6 Problems 271

6.7 References 278

Chapter 7 Thiazoles and Benzothiazoles 283

7.1 Introduction 283

7.2 Reactions of the Thiazole Ring 290 ix

7.3 Palladium Chemistry Undergone by Thiazoles and Benzothiazoles 300

7.4 Construction of the Thiazole Ring 307

7.5 Construction of the Benzothiazole Ring 315

7.6 Possible Liabilities of Drugs Containing Thiazoles and Benzothiazoles 321

7.7 Thiazoles and Benzothiazoles as Bioisosteres 323

7.8 Problems 325

7.9 References 328

Chapter 8 Imidazoles and Benzimidazoles 333

8.1 Introduction to Imidazole 333

8.2 Reactivity of the Imidazole Ring 335

8.3 Construction of the Imidazole Ring 341

8.3.1 Debus 342

8.4 Conversion of Imidazolines to Imidazoles 353

8.5 Possible Liabilities of Imidazole-Containing Drugs 353

8.6 Introduction to Benzimidazole 354

8.7 Synthesis of Benzimidazoles: Classical Approaches 357

8.8 Construction of the Benzimidazole Core Using Transition Metal- Mediated Approaches 361

8.9 Alternative Cyclization Approach toward Benzimidazoles: Process Route toward BYK405879 367

8.10 Problems 368

8.11 References 370

Chapter 9 Triazoles and Tetrazoles 373

9.1 Introduction 373

9.2 Reactivity of the Triazole and Tetrazole Ring 375

9.3 Construction of the Triazole Ring 384

9.4 Possible Liabilities of Triazole-Containing Drugs 392

9.5 Problems 393

9.6 References 394

PART III SIX-MEMBERED HETEROCYCLES WITH ONE HETEROATOM 397

Chapter 10 Pyridines 398

10.1 Introduction 398

10.2 Reactivity of the Pyridine Ring 404

10.3 Construction of the Pyridine Ring 425

10.4. Problems 457

10.5 References 459

Chapter 11 Quinolines and Isoquinolines 471

11.1 Introduction 471

11.2 Reactivity of the Quinoline and Isoquinoline Ring 474

11.3 Construction of Quinoline Core 492

11.4 Construction of Isoquinoline Core 513

11.5 Possible Liabilities of Drugs Containing Quinoline and Isoquinoline Ring 526

11.6 Problems 527

11.7 References 528

PART IV SIX-MEMBERED HETEROCYCLES WITH TWO HETEROATOMS 535

Chapter 12 Pyrazines and Quinoxalines 536

12.1 Introduction 536

12.2 Formation of Diazines 539

12.3 Reactivity of the Molecules 545

12.4 Coupling Reactions 553

12.5 Problems 562

12.6 References 565

Chapter 13 Pyrimidines 569

13.1 Introduction 569

13.2 Construction of the Pyrimidine Ring 573

13.3 Synthesis of Pyrimidine-Containing Drugs 590

13.4 Problems 608

13.5 References 611

Chapter 14 Quinazolines and Quinazolones 615

14.1 Introduction 615

14.2 Reactions of Quinazolines and Quinazolinones 618

14.3 Quinazoline and Quinazolinone Synthesis 625

14.4 Synthesis of Quinazoline- and Quinazolinone-Containing Drugs 636

14.5 Problems 641

14.6 References 644

Subject Index 647



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