Pyridines: from lab to production - 1st Edition - ISBN: 9780123852359, 9780123852366

Pyridines: from lab to production

1st Edition

Editors: Eric F.V. Scriven
Hardcover ISBN: 9780123852359
eBook ISBN: 9780123852366
Imprint: Academic Press
Published Date: 22nd January 2013
Page Count: 582
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Table of Contents

Best Synthetic Methods

Other volumes in the Series

Preface

Contributors

Chapter 1. Introduction

1 Introduction

2 Value Chains

3 Strategic Considerations – Ring Synthesis Vs Substituent Manipulation

4 Challenges and Needs

References

Chapter 2. Ring Synthesis

1 Introduction

2 By the Formation of One Bond

3 By the Formation of Two Bonds

4 By the Formation of Three Bonds

5 Formation of Four Bonds

6 Transformations from Other Rings

7 Formal Exchange of Ring Members

8 Aromatisation

9 From Larger Molecules

References

Chapter 3. Attachment at Ring Positions

1 Introduction

2 Halogen

3 Sulphur and Selenium

4 Silicon

5 Tin

6 Phosphorus

7 Oxygen

8 Boron

9 Nitrogen

10 Carbon

11 Lithium

12 Magnesium

13 Zinc

14 Conclusion

References

Chapter 4. Substituent Modifications

1 Introduction

2 Carbon-Linked Substituents (Pyr-C)

4.3 Nitrogen-Linked Substituents (Pyr-N)

4.4 Oxygen-Linked Substituents (Pyr-O)

4.5 Sulphur-Linked Substituents (Pyr-S)

4.6 Halogen Linked to Ring (Pyr-halogen)

4.7 Substituents on the Ring Nitrogen (PyrN+-X)

References

Chapter 5. Formation of Completely or Partially Reduced Pyridines and Quinolines

1 Introduction

2 Preparation of Piperidine and Substituted Piperidines

3 Preparation of Saturated Quinolines

4 Biologically Active Piperidine and Tetrahydroquinoline compounds

References

Chapter 6. Applications to Alkaloid Synthesis

1 Introduction

2 Alkaloid Synthesis

3 Summary

References

Chapter 7. Fluorinated Pyridines

1 Fluoropyridines

2 Trifluoromethylpyridines

3 Conclusions

References

Chapter 8. Pyridine-Containing Reagents

1 Introduction

2 2-(Dimethylamino)pyridine (1)

3 4-(Dimethylamino)pyridine (12)

4 Tetrakis(pyridine-2-yloxy)silane (26) as a Coupling Reagent in the Synthesis of Carboxamides

5 2-Benzyloxy-1-methylpyridinium triflate (Dudley Reagent, 30)

6 (2S)-2-[(2-Pyridyloxy)methyl]pyrrolidine (37) as Catalyst for Enantioselective Michael Addition to Nitro Olefins

References

Chapter 9. Synthesis of Heterocyclic Compounds Using Continuous Flow Reactors

1 Introduction

2 Practical Implications in the Development of Continuous Processes

3 Heterocyclic Synthesis in Continuous Flow Reactors

4 Conclusion

References

Index


Description

Best Synthetic Methods

Other volumes in the Series

Preface

Contributors

Chapter 1. Introduction

1 Introduction

2 Value Chains

3 Strategic Considerations – Ring Synthesis Vs Substituent Manipulation

4 Challenges and Needs

References

Chapter 2. Ring Synthesis

1 Introduction

2 By the Formation of One Bond

3 By the Formation of Two Bonds

4 By the Formation of Three Bonds

5 Formation of Four Bonds

6 Transformations from Other Rings

7 Formal Exchange of Ring Members

8 Aromatisation

9 From Larger Molecules

References

Chapter 3. Attachment at Ring Positions

1 Introduction

2 Halogen

3 Sulphur and Selenium

4 Silicon

5 Tin

6 Phosphorus

7 Oxygen

8 Boron

9 Nitrogen

10 Carbon

11 Lithium

12 Magnesium

13 Zinc

14 Conclusion

References

Chapter 4. Substituent Modifications

1 Introduction

2 Carbon-Linked Substituents (Pyr-C)

4.3 Nitrogen-Linked Substituents (Pyr-N)

4.4 Oxygen-Linked Substituents (Pyr-O)

4.5 Sulphur-Linked Substituents (Pyr-S)

4.6 Halogen Linked to Ring (Pyr-halogen)

4.7 Substituents on the Ring Nitrogen (PyrN+-X)

References

Chapter 5. Formation of Completely or Partially Reduced Pyridines and Quinolines

1 Introduction

2 Preparation of Piperidine and Substituted Piperidines

3 Preparation of Saturated Quinolines

4 Biologically Active Piperidine and Tetrahydroquinoline compounds

References

Chapter 6. Applications to Alkaloid Synthesis

1 Introduction

2 Alkaloid Synthesis

3 Summary

References

Chapter 7. Fluorinated Pyridines

1 Fluoropyridines

2 Trifluoromethylpyridines

3 Conclusions

References

Chapter 8. Pyridine-Containing Reagents

1 Introduction

2 2-(Dimethylamino)pyridine (1)

3 4-(Dimethylamino)pyridine (12)

4 Tetrakis(pyridine-2-yloxy)silane (26) as a Coupling Reagent in the Synthesis of Carboxamides

5 2-Benzyloxy-1-methylpyridinium triflate (Dudley Reagent, 30)

6 (2S)-2-[(2-Pyridyloxy)methyl]pyrrolidine (37) as Catalyst for Enantioselective Michael Addition to Nitro Olefins

References

Chapter 9. Synthesis of Heterocyclic Compounds Using Continuous Flow Reactors

1 Introduction

2 Practical Implications in the Development of Continuous Processes

3 Heterocyclic Synthesis in Continuous Flow Reactors

4 Conclusion

References

Index

Key Features

  • Reviews tried and tested practical methods to help the reader select the best method for their research
  • Includes tips, tricks and hints to enable the reader to get the best yield or cleanest product out of their reaction for synthesising or transforming a pyridine derivative
  • Written by both academic researchers and industry leaders this provides a unique view of how to get the most out of a reaction no matter what scale you are running this on

Readership

A reference book for organic and pharmaceutical chemists and for those interested in the synthesis and manufacture of pyridine and its derivatives including those working in the polymer and material sciences. It is also appropriate as a reference book for the practical classes on synthetic organic chemistry.


Details

No. of pages:
582
Language:
English
Copyright:
© Academic Press 2013
Published:
Imprint:
Academic Press
eBook ISBN:
9780123852366
Hardcover ISBN:
9780123852359

Reviews

"Editor Scriven…presents this comprehensive reference for academics and industrialists working in the synthesis of pyridine derivatives. Strategic considerations for economizing reagents are discussed in the introduction; in particular, the question of whether to install substituents before or after cyclization is highlighted."--Reference & Research Book News, October 2013


About the Editors

Eric F.V. Scriven Editor

Eric Scriven was educated in the UK and appointed lecturer in organic chemistry at the University of Salford in 1971. He joined Reilly Industries in 1979, and was Head of Research & Development 1991-2003. He is now Publishing Editor of Arkivoc and is based at the Department of Chemistry, University of Florida in Gainesville. His research interests are in heterocyclic chemistry, especially pyridines. He has over 100 publications and patents in heterocyclic chemistry. He has also published and consulted in the field of technology management. He was a founding editor (with Hans Suschitzky) of Progress in Heterocyclic Chemistry now in its 25th year. He has collaborated with Alan Katritzky and others as an Editor-in-Chief of Comprehensive Heterocyclic Chemistry 2nd and 3rd editions. He has edited two other works, Azides and Nitrenes (1984), and Pyridines (2013).

Affiliations and Expertise

University of Florida, Gainesville, FL, USA