 |
Green synthetic approaches for biologically relevant heterocycles / edited by Goutam Brahmachari. -- Waltham, MA : Elsevier, c2014. – (54.556/G798) |
Contents
Contents
Contributors xiii
About the Editor xv
Foreword xvii
Preface xix
1. Green Synthetic Approaches for Biologically Relevant Heterocycles: An Overview
GOUTAM BRAHMACHARI
1. Introduction 1
2. An Overview of the Book 2
3. Concluding Remarks 6
2. Synthesis of Bioactive Five- and Six， Membered Heterocycles Catalyzed by Heterogeneous Supported Metals
BR1NDABAN C. RANU， TANMAY CHATTERJEE， N1RMALYA MUKHERJEE， PINTU MAITY AND BIJU MAJHI
1. Introduction 7
2. Synthesis of N-Containing Heterocycles 8
3. Synthesis of Oxygen-Containing Heterocycles 28
4. Synthesis of Sulfur-Containing Heterocycles 36
5. Concluding Remarks 40
References 40
3. Transition-Metal-Free Synthesis of Benzo-Fused Five- and Six-Membered Heterocycles Employing Arynes
TRINADH KAICHARLA AND AKKATTU T. BIJU
1. Introduction 46
2. Synthesis of Five-Membered Heterocycles 47
3. Synthesis of Six-Membered Heterocycles 60
4. Synthesis of Medium-Sized Heterocycles 71
5. Applications of the Benzo-Fused Heterocycles 72
6. Concluding Remarks 73
References 73
4. Metal-Catalyzed Routes for the Synthesis of Furocoumarins and Coumestans
VICTORIO CADIERNO
1. Introduction 77
2. Synthetic Routes to Furocoumarin Derivatives 78
3. Synthetic Routes to Coumestan Derivatives 90
4. Concluding Remarks 96
Acknowledgments 96
References 96
5. Green Solvents for Eco-friendly Synthesis of Bioactive Heterocyclic Compounds
ANTON V. DOLZHENKO AND ANNA V. DOLZHENKO
1. Introduction 101
2. Heterocyclic Synthesis in Supercritical Carbon Dioxide 102
3. Heterocyclic Synthesis in PEG 108
4. Heterocyclic Synthesis in Glycerol 126
5. Heterocyclic Synthesis in Gluconic Acid Aqueous Solution 130
6. Heterocyclic Synthesis in Ethyl Lactate 133
7. Concluding Remarks 134
References 134
6. Green Catalytic Synthesis of Heterocyclic Structures Using Carbon Dioxide and Related Motifs
ARJAN W. KLEII
1. Introduction
2. Biological Importance of CO2-Based Heterocyclic Compounds
3. Green Synthesis of 1，3-Dioxolan-2-Ones and 1，3-Dioxan-2-Ones Using CO2
4. Green Synthesis of Oxazolidinones and Oxazodinanones Using CO2
5. Related Heterocycles Incorporating CO2 or Related Synthons
6. Concluding Remarks
References
7. Synthetic Approaches to Small- and Medium-Size Aza-Heterocycles in Aqueous Media
GIRIJA S. SINGH AND TUMELO H. TABANE
1. Introduction 163
2. Three-Membered Ring--Aziridines 164
3. Four-Membered Rings 165
4. Five-Membered Rings 168
5. Six-Membered Rings 176
6. Seven-Membered Rings 179
7. Concluding Remarks 181
References 181
8. Green Synthetic Approaches for Biologically Relevant 2-amino-4H-pyrans and 2-amino-4H-pyran-Annulated Heterocycles in Aqueous Media
GOUTAM BRAHMACHARI
1. Introduction 185
2. Synthetic Approaches for 2-amino-4H-pyrans and 2-amino-4H-pyran-Annulated Heterocycles in Water and Ethanol-Water Media 186
3. Concluding Remarks 203
Acknowledgments 204
References 204
9. Sustainable Synthesis of Benzimidazoles， Quinoxalines， and Congeners
BASUDEB BASU AND BABLEE MANDAL
1. Introduction 209
2. Methods of Synthesis of Benzimidazoles/Quinoxalines Using Greener Strategies 211
3. Concluding Remarks 251
References 252
10. Green and Catalytic Methods for γ，-Lactone Synthesis
HIKARU YANAI
1. Introduction
2. Constructive Methods for γ-Lactone Structure
3. Functionalization of γ-Lactone Structures
4. Concluding Remarks
References
11. Green Synthetic Approaches for Medium Ring-Sized Heterocycles of Biological Interest
SHITAL K. CHATTOPADHYA
1. Introduction 291
2. Microwave- and Ultrasound-Assisted Synthesis of Medium Ring-Sized Heterocycles 294
3. Use of Ionic Liquids as Reaction Medium and Catalyst 302
4. Use of Environmentally Benign Solvents 304
5. Use of Heterogeneous Catalysis 308
6. Fluorous Synthesis 309
7. Concluding Remarks 310
References 311
12. Organocatalyzed Biginelli Reactions: A Greener Chemical Approach for the Synthesis of Biologically Active 3，4-Dihydropyrimidin-2(1H)-ones/-thiones
ANGELO DE FfiIT1MA， BRUNA SILVA TERRA， LEONARDO DA SILVA NETO AND TANIRIS CAFIERO BRAGA
1. Introduction
2. Classes of Organocatalysts Used in the Biginelli Reaction 320
3. Biological Significance of 3，4-Dihydropyrimidin-2(1H)-ones/-thiones 332
4. Concluding Remarks 334
Abbreviations 334
Acknowledgments 335
References 335
13. Photocatalytic Minisci Reaction: A Promising and Eco-friendly Route to Functionalize Heteroaromatics of Biological Interest
CRISTIAN GAMBAROTTI， LUC10 MELONE， CARLO PUNTA AND G1USEPPINA RAFFAINI
1. Introduction 339
2. Minisci Reaction: A Versatile Tool for Medicinal Chemistry
3. Minisci Reaction: The General Mechanism
4. The Photocatalytic Approach
5. Is it a Green Approach?
6. Molecular Dynamics Studies: Toward the Solut
7. Concluding Remarks
Acknowledgments
References
14. Organohypervalent Iodine Reagents in the Synthesis of Bioactive Heterocycles
DALIP KUMAR， V. ARUN， MEENAKSHI PILANIA AND N. MARUTHI KUMAR
1. Introduction
2. Organohypervalent Iodine Promoted Synthesis of Bioactive Heterocycles 357
3. Concluding Remarks 374
Abbreviations 374
References 374
15. Porous Catalytic Systems in the Synthesis of Bioactive Heterocycles and Related Compounds
ELENA PEREZ-MAYORAL， VANESA CALVINO-CAS1LDA， MARINA GODINO， ANTONIO J. LOPEZ- PEINADO AND ROSA M. MARTIN-ARANDA
1. Introduction
2. Porous Catalytic Systems
3. Synthesis of Bioactive Heterocycle by Porous Materials
4. Concluding Remarks
Acknowledgment
References
16. High-Pressure Cycloaddition Reactions in the Synthesis of Biologically Relevant Heterocycles
DAVOR MARGETIC
1. Introduction 409
2. Diels-Alder Cycloadditions 410
3. Dipolar Cycloadditions 430
4. [2 + 2] Cycloadditions 432
5. Concluding Remarks 432
Abbreviations 432
References 433
17. Ionic Liquids-Prompted Synthesis of Biologically Relevant Five- and Six-Membered Heterocyclic Skeletons: An Update
BHUWAN B. MISHRA， DHANANJAY KUMAR， ANOOP S. S1NGH， RAMA P. TRIPATHI AND VINOD K. TIWARI
1. Introduction
2. Properties of ILs
3. Recent Developments in Ionic Liquids Research
4. Application of Ionic Liquids in Heterocyclic Synthesis
5. Concluding Remarks
Acknowledgments
References
18. Heterocycles-Based Ionic Liquid-Supported Synthesis of Small Organic Molecules
VIJAYKUMAR V. PAIKE AND CHUNG-M1NG SUN
1. Introduction
2. Ionic Liquid-Supported Synthesis of Small Molecules
3. Ionic Liquid-Supported Carbohydrate Synthesis
4. Ionic Liquid-Supported Peptide Synthesis
5. Ionic Liquid-Supported Reagents
6. Ionic Liquid-Supported Catalysts
7. Concluding Remarks
Abbreviations
References
19. Microwave-Induced Synthesis of Heterocycles of Medicinal Interests
DEBASISH BANDYOPADHYAY AND BIMAL K. BANIK
1. Introduction
2. Microwave Irradiation: Mechanism
3. Microwave-Induced Synthesis of Heterocycles of Medicinal Interests
4. Concluding Remarks
Abbreviations
References
20. Application of Microwave Irradiation in the Synthesis of P-Heterocycles
GYORGY KEGLEVICH
1. Introduction 559
2. Functionalization of Cyclic Phosphinic Acids 560
3. Diels-Alder Cycloadditions， Fragmentation-Related Phosphorylations， and Inverse Wittig-Type Reactions 563
4. Phospha-Michael Reactions 564
5. Kabachnik-Fields Reactions 566
6. Concluding Remarks 568
References 568
21. Use of Ultrasound in the Synthesis of Heterocycles of Medicinal Interest
MAR1A A. SCHIEL， AL1CIA B. CHOPA， GUSTAVO E SILBESTRI， MONICA B. ALVAREZ， ADRIANA G. LISTA AND CLAUDIA E. DOMINI
Index
