Multicomponent Reactions in Organic Synthesis E-Book

• Herausgeber: Wiley-VCH
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 634

Veröffentlichungsjahr: 2014

Beschreibung

Comprehensive and up-to-date, this book focuses on the latest advances in the field, such as newly developed techniques, more environmentally benign processes, broadened scopes, and completely novel MCRs. In addition to carbene-promoted MCRs and frequently applied metal-catalyzed MCRs, it also covers recently developed catalytic enantioselective variants as well as MCR in drug discovery and for the synthesis of heterocyclic molecules and macrocycles. Edited by the leading experts and with a list of authors reading like a "who's who" in multicomponent reaction chemistry, this is definitely a must-have for every synthetic organic chemist as well as medicinal chemists working in academia and pharmaceutical companies.

Leseprobe

CONTENTS

Cover

Related Titles

Title Page

Copyright

Preface

List of Contributors

Chapter 1: General Introduction to MCRs: Past, Present, and Future

1.1 Introduction

1.2 Advances in Chemistry

1.3 Total Syntheses

1.4 Applications in Pharmaceutical and Agrochemical Industry

1.5 Materials

1.6 Outlook

References

Chapter 2: Discovery of MCRs

2.1 General Introduction

2.2 The Concept

2.3 The Reaction Design Concept

2.4 Multicomponent Reactions and Biocatalysis

2.5 Multicomponent Reactions in Green Pharmaceutical Production

2.6 Conclusions

Acknowledgments

References

Chapter 3: Aryne-Based Multicomponent Reactions

3.1 Introduction

3.2 Multicomponent Reactions of Arynes via Electrophilic Coupling

3.3 Transition Metal-Catalyzed Multicomponent Reactions of Arynes

3.4 Concluding Remarks

References

Chapter 4: Ugi–Smiles and Passerini–Smiles Couplings

4.1 Introduction

4.2 Scope and Limitations

4.3 Ugi–Smiles Postcondensations

4.4 Conclusions

References

Chapter 5: 1,3-Dicarbonyls in Multicomponent Reactions

5.1 Introduction

5.2 Achiral and Racemic MCRs

5.3 Enantioselective MCRs

5.4 Conclusions and Outlook

References

Chapter 6: Functionalization of Heterocycles by MCRs

6.1 Introduction

6.2 Mannich-Type Reactions and Related Processes

6.3 β-Dicarbonyl Chemistry

6.4 Hetero-Diels–Alder Cycloadditions and Related Processes

6.5 Metal-Mediated Processes

6.6 Isocyanide-Based Reactions

6.7 Dipole-Mediated Processes

6.8 Conclusions

Acknowledgments

References

Chapter 7: Diazoacetate and Related Metal-Stabilized Carbene Species in MCRs

7.1 Introduction

7.2 MCRs via Carbonyl or Azomethine Ylide-Involved 1,3-Dipolar Cycloadditions

7.3 MCRs via Electrophilic Trapping of Protic Onium Ylides

7.4 MCRs via Electrophilic Trapping of Zwitterionic Intermediates

7.5 MCRs via Metal Carbene Migratory Insertion

7.6 Summary and Outlook

References

Chapter 8: Metal-Catalyzed Multicomponent Synthesis of Heterocycles

8.1 Introduction

8.2 Multicomponent Cross-Coupling and Carbonylation Reactions

8.3 Metallacycles in Multicomponent Reactions

8.4 Multicomponent Reactions via 1,3-Dipolar Cycloaddition

8.5 Concluding Remarks

References

Chapter 9: Macrocycles from Multicomponent Reactions

9.1 Introduction

9.2 IMCR-Based Macrocyclizations of Single Bifunctional Building Blocks

9.3 Multiple MCR-Based Macrocyclizations of Bifunctional Building Blocks

9.4 IMCR-Based Macrocyclizations of Trifunctionalized Building Blocks (MiB-3D)

9.5 Sequential IMCR-Based Macrocyclizations of Multiple Bifunctional Building Blocks

9.6 Final Remarks and Future Perspectives

References

Chapter 10: Multicomponent Reactions under Oxidative Conditions

10.1 Introduction

10.2 Multicomponent Reactions Involving In Situ Oxidation of One Substrate

10.3 Multicomponent Reactions Involving Oxidation of a Reaction Intermediate

10.4 Multicomponent Reactions Involving Oxidants as Lewis Acids

10.5 Conclusions

References

Chapter 11: Allenes in Multicomponent Synthesis of Heterocycles

11.1 Introduction

11.2 Reactions with 1,2-Propadiene and Unactivated Allenes

11.3 Reactions with Acceptor-Substituted Allenes

11.4 Reactions with Donor-Substituted Allenes

11.5 Conclusions

List of Abbreviations

References

Chapter 12: Alkynes in Multicomponent Synthesis of Heterocycles

12.1 Introduction

12.2 σ-Nucleophilic Reactivity of Alkynes

12.3 π-Nucleophilic Reactivity of Alkynes

12.4 Alkynes as Electrophilic Partners

12.5 Alkynes in Cycloadditions

12.6 Alkynes as Reaction Partners in Organometallic MCRs

12.7 Conclusions

List of Abbreviations

Acknowledgment

References

Chapter 13: Anhydride-Based Multicomponent Reactions

13.1 Introduction

13.2 Quinolones and Related Heterocycles from Homophthalic and Isatoic Anhydrides

13.3 α,β-Unsaturated Cyclic Anhydrides: MCRs Involving Conjugate Addition and Cycloaddition Reactions

13.4 MCRs of Cyclic Anhydrides in Annulation Reactions and Related Processes

13.5 MCRs of Acyclic Anhydrides

13.6 Conclusions

References

Chapter 14: Free-Radical Multicomponent Processes

14.1 Introduction

14.2 MCRs Involving Addition Across Olefin C=C Bonds

14.3 Free-Radical Carbonylation

14.4 Free-Radical Oxygenation

14.5 MCRs Involving Addition Across π-C=N Bonds

14.6 Miscellaneous Free-Radical Multicomponent Reactions

14.7 Conclusions

References

Chapter 15: Chiral Phosphoric Acid-Catalyzed Asymmetric Multicomponent Reactions

15.1 Introduction

15.2 Mannich Reaction

15.3 Ugi-Type Reaction

15.4 Biginelli Reaction

15.5 Aza-Diels–Alder Reaction

15.6 1,3-Dipolar Cycloaddition

15.7 Hantzsch Dihydropyridine Synthesis

15.8 The Combination of Metal and Chiral Phosphoric Acid for Multicomponent Reaction

15.9 Other Phosphoric Acid-Catalyzed Multicomponent Reactions

15.10 Summary

References

Index

End User License Agreement

List of Tables

Table 4.1

Table 4.2

Table 9.1

Table 10.1

Table 10.2

Table 13.1

Table 13.2

Table 13.3

List of Illustrations

Figure 1.1

Figure 1.2

Figure 1.3

Figure 1.4

Figure 1.5

Figure 1.6

Figure 1.7

Figure 1.8

Figure 2.1

Scheme 2.1

Figure 2.2

Figure 2.3

Scheme 2.2

Scheme 2.3

Scheme 2.4

Scheme 2.5

Figure 2.4

Scheme 2.6

Scheme 2.7

Scheme 2.8

Scheme 2.9

Scheme 2.10

Scheme 2.11

Scheme 2.12

Scheme 2.13

Scheme 2.14

Scheme 2.15

Scheme 2.16

Scheme 2.17

Figure 3.1

Scheme 3.1

Figure 3.2

Scheme 3.2

Scheme 3.3

Scheme 3.4

Scheme 3.5

Scheme 3.6

Scheme 3.7

Scheme 3.8

Scheme 3.9

Scheme 3.10

Scheme 3.11

Scheme 3.12

Scheme 3.13

Scheme 3.14

Scheme 3.15

Scheme 3.16

Scheme 3.17

Scheme 3.18

Scheme 3.19

Scheme 3.20

Scheme 3.21

Scheme 3.22

Scheme 3.23

Scheme 3.24

Scheme 3.25

Scheme 3.26

Scheme 3.27

Scheme 3.28

Scheme 3.29

Scheme 3.30

Scheme 3.31

Scheme 3.32

Scheme 3.33

Scheme 3.34

Scheme 3.35

Scheme 3.36

Scheme 3.37

Scheme 3.38

Scheme 3.39

Scheme 3.40

Scheme 3.41

Scheme 3.42

Scheme 3.43

Scheme 3.44

Scheme 3.45

Scheme 3.46

Scheme 3.47

Scheme 3.48

Scheme 3.49

Scheme 4.1

Scheme 4.2

Scheme 4.3

Scheme 4.4

Scheme 4.5

Scheme 4.6

Scheme 4.7

Scheme 4.8

Scheme 4.9

Scheme 4.10

Scheme 4.11

Figure 4.1

Figure 4.2

Scheme 4.12

Scheme 4.13

Scheme 4.14

Scheme 4.15

Scheme 4.16

Scheme 4.17

Scheme 4.18

Scheme 4.19

Scheme 4.20

Scheme 4.21

Scheme 4.22

Scheme 4.23

Scheme 4.24

Scheme 4.25

Scheme 4.26

Scheme 4.27

Scheme 4.28

Scheme 4.29

Scheme 4.30

Scheme 4.31

Scheme 4.32

Scheme 4.33

Scheme 4.34

Scheme 4.35

Scheme 4.36

Scheme 4.37

Scheme 4.38

Scheme 4.39

Scheme 4.40

Scheme 4.41

Scheme 4.42

Scheme 4.43

Scheme 4.44

Scheme 4.45

Scheme 4.46

Scheme 4.47

Scheme 4.48

Scheme 4.49

Scheme 4.50

Scheme 4.51

Scheme 4.52

Scheme 4.53

Scheme 4.54

Scheme 4.55

Scheme 4.56

Scheme 4.57

Scheme 4.58

Figure 5.1

Scheme 5.1

Figure 5.2

Scheme 5.2

Scheme 5.3

Scheme 5.4

Scheme 5.5

Scheme 5.6

Scheme 5.7

Scheme 5.8

Scheme 5.9

Scheme 5.10

Figure 5.3

Scheme 5.11

Scheme 5.12

Scheme 5.13

Scheme 5.14

Scheme 5.15

Scheme 5.16

Scheme 5.17

Scheme 5.18

Scheme 5.19

Scheme 5.20

Scheme 5.21

Scheme 5.22

Scheme 5.23

Scheme 5.24

Scheme 5.25

Scheme 5.26

Scheme 5.27

Scheme 5.28

Scheme 5.29

Scheme 5.30

Scheme 5.31

Scheme 5.32

Scheme 5.33

Scheme 5.34

Scheme 5.35

Scheme 5.36

Scheme 5.37

Scheme 5.38

Scheme 5.39

Scheme 5.40

Scheme 5.41

Scheme 5.42

Scheme 5.43

Scheme 5.44

Scheme 5.45

Scheme 5.46

Scheme 5.47

Figure 5.4

Scheme 5.48

Scheme 5.49

Scheme 5.50

Scheme 5.51

Scheme 5.52

Scheme 5.53

Scheme 5.54

Scheme 5.55

Figure 5.5

Scheme 5.56

Scheme 5.57

Scheme 5.58

Scheme 5.59

Scheme 5.60

Scheme 5.61

Scheme 5.62

Scheme 5.63

Scheme 5.64

Scheme 5.65

Scheme 5.66

Scheme 5.67

Scheme 5.68

Figure 5.6

Scheme 5.69

Scheme 5.70

Scheme 5.71

Scheme 5.72

Figure 5.7

Scheme 5.73

Scheme 5.74

Scheme 6.1

Scheme 6.2

Scheme 6.3

Scheme 6.4

Scheme 6.5

Scheme 6.6

Scheme 6.7

Scheme 6.8

Scheme 6.9

Scheme 6.10

Scheme 6.11

Scheme 6.12

Scheme 6.13

Scheme 6.14

Scheme 6.15

Scheme 6.16

Scheme 6.17

Scheme 6.18

Scheme 6.19

Scheme 6.20

Scheme 6.21

Scheme 6.22

Scheme 6.23

Scheme 6.24

Scheme 6.25

Scheme 6.26

Scheme 7.1

Scheme 7.2

Scheme 7.3

Scheme 7.4

Scheme 7.5

Scheme 7.6

Scheme 7.7

Scheme 7.8

Scheme 7.9

Scheme 7.10

Scheme 7.11

Scheme 7.12

Scheme 7.13

Scheme 7.14

Scheme 7.15

Scheme 7.16

Scheme 7.17

Scheme 7.18

Scheme 7.19

Scheme 7.20

Scheme 7.21

Scheme 7.22

Scheme 7.23

Scheme 7.24

Scheme 7.25

Scheme 7.26

Scheme 7.27

Scheme 7.28

Scheme 7.29

Scheme 7.30

Scheme 8.1

Scheme 8.2

Scheme 8.3

Scheme 8.4

Scheme 8.5

Scheme 8.6

Scheme 8.7

Scheme 8.8

Scheme 8.9

Scheme 8.10

Scheme 8.11

Scheme 8.12

Scheme 8.13

Scheme 8.14

Scheme 8.15

Scheme 8.16

Scheme 8.17

Scheme 8.18

Scheme 8.19

Scheme 8.20

Scheme 8.21

Scheme 8.22

Scheme 8.23

Scheme 8.24

Scheme 8.25

Scheme 8.26

Scheme 8.27

Scheme 8.28

Scheme 8.29

Scheme 8.30

Scheme 8.31