Chemistry of Bipyrazoles: Synthesis and Applications covers the synthetic pathways for all types of bipyrazoles. 5 chapters cover bipyrazole systems, N,N- and N,C-bipyrazoles, namely 1,1`-bipyrazole, 1,3`-bipyrazole, 1,4`-bipyrazole, 3,3`-bipyrazoles, 3,4`-bipyrazoles and 4,4`-bipyrazoles
The contents explain several types of reactions: 1) condensation reactions of hydrazines with tetracarbonyls, dihydroxydicarbonyl compounds or pyrazole-based difunctional compounds; 2) 1,3-dipolar cycloaddition of pyrazole-based hydrazonoyl halides with activated methylene compounds; 3) metal catalyzed cross-coupling reactions.
The book concludes with a chapter that details the applications of bipyrazole derivatives in different industries. Information about advanced concepts used in chemical engineering such as metal-organic frameworks (MOFs) and corrosion inhibition are highlighted.
The book contents are presented in an easy-to-understand manner suitable for readers in organic chemistry at senior levels of education and industry expertise. Each chapter is supplemented with detailed references.

Pyrazole is one of the most valuable nitrogen-based heterocycles and is incorporated in the constitution of a wide range of pharmaceuticals and agrochemicals. Direct connection of two pyrazole units produces six different bipyrazole skeletons that can be classified as i) N-N bond connected 1,1`-bipyrazoles; ii) C-N bond connected 1,3`- and 1,4`-bipyrazoles and iii) C-C bond connected 3,3`-, 3,4`- and 4,4`-bipyrazoles.
This book presents the recent achievements in the synthetic platforms toward the directly connected bipyrazole systems and their applications in academic, industrial, and material science fields. The construction of the targeted bipyrazole heterocycles was carried out via a wide-range of synthetic routes that grasp the attention of graduate and postgraduate chemists and pharmacists and material science researchers to make more efforts in this area to reach high impact findings for their applications in our life.
Most of the reported bipyrazoles are highly bioactive heterocycles demonstrating a broad array of significant inhibitory activities against several human diseases and agricultural pesticides and herbicides. They also have considerable applications in the material science area via involvement in the construction of metal-organic frameworks (MOFs) with distinguished industrial applications.
This book is presented in five chapters describing the synthesis of six connected bipyrazole systems and their brilliant and vibrant applications. As a result, we expect that the provided book chapters will be of pronounced support and a valuable source for the scientific community for developing new bipyrazole-based fascinating candidates towards optimization of their pharmacological benefits in the treatment of diseases as well as building up new MOFs for daily life applications that serve the humanity and industry.
We hope that the researchers and readers will find new ideas based on the provided work. Finally, we are very thankful to the Bentham Science Publishers for giving us the chance to publish this book.
CONSENT FOR PUBLICATION
Not applicable.
CONFLICT OF INTEREST
The authors declare that there is no conflict of interest.
ACKNOWLEDGEMENT
Declared none.
Kamal M. Dawood & Ashraf A. Abbas
Department of Chemistry, Faculty of Science,
Cairo University
Giza 12613, Egypt

PREFACE i

CONSENT FOR PUBLICATION i

CONFLICT OF INTEREST i

ACKNOWLEDGEMENTS i

CHAPTER 1 CHEMISTRY OF N,N- AND C,N-LINKED BIPYRAZOLE DERIVATIVES 1

1. INTRODUCTION 1

2. SYNTHESIS OF BIPYRAZOLE SYSTEMS 2

      2.1. Synthesis of 1,1`-Bipyrazoles 2

      2.2. Synthesis of 1,3`-bipyrazoles 3

      2.3. Synthesis of 1,4`-bipyrazoles 12

CONCLUSION 17

REFERENCES 17

CHAPTER 2 CHEMISTRY OF 3.3`-BIPYRAZOLE DERIVATIVES 22

1. INTRODUCTION 22

2. SYNTHESIS OF 3,3`-BIPYRAZOLE SYSTEMS 24

      2.1. From 1,3-Dipolar Cycloaddition Reactions 24

      2.2. Via Cyclocondensation Reactions 34

      2.3. From Metal Catalyzed C-H Activation Reactions 45

3. REACTIONS OF 3,3`-BIPYRAZOLE DERIVATIVES 46

      3.1. Nitration of 3,3`-Bipyrazole Derivatives 46

      3.2. Miscellaneous Reactions 50

CONCLUSION 51

REFERENCES 52

CHAPTER 3 CHEMISTRY OF 3,4`-BIPYRAZOLES 57

1. INTRODUCTION 57

2. SYNTHESIS OF 3,4`-BIPYRAZOLE DERIVATIVES 59

      2.1. From 1,3-dipolar Cycloaddition Reactions 59

      2.2. From Cyclocondensation of 4-pyrazolylchalcones 63

      2.3. From Cyclocondensation of 4-pyrazolyl-bifunctional Side-arm with Hydrazines 77

      2.4. From C-C Cross Coupling Between Two Pyrazole Units 90

CONCLUSION 91

REFERENCES 91

CHAPTER 4 CHEMISTRY OF 4,4`-BIPYRAZOLES 100

1. INTRODUCTION 100

2. SYNTHESIS OF 4,4`-BIPYRAZOLE DERIVATIVES 102

      2.1. From Dimerization of Pyrazoles 102

      2.2. From 1,3-dipolar Cycloaddition 105

      2.3. From Functionalized Pyrazoles 106

CONCLUSION 110

REFERENCES 111

CHAPTER 5 APPLICATIONS OF BIPYRAZOLE DERIVATIVES 114

1. INTRODUCTION 114

2. APPLICATIONS OF BIPYRAZOLE DERIVATIVES 114

      2.1. Bipyrazoles as Ligands 114

      2.2. Bipyrazoles in Synthesis of Polybipyrazoles 116

      2.3. Bipyrazoles as Energetic Materials 117

      2.4. Bipyrazoles as Corrosion Inhibitors 120

      2.5. Bipyrazoles as Therapeutics 121

      2.6. Bipyrazoles in Metal-organic Frameworks (MOFs) 122

CONCLUSION 136

REFERENCES 137

SUBJECT INDEX 145

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