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Green Synthetic Approaches for Biologically Relevant Heterocycles

1st Edition - November 8, 2014

Editor: Goutam Brahmachari

Hardback ISBN:

9 7 8 - 0 - 1 2 - 8 0 0 0 7 0 - 0

Paperback ISBN:

9 7 8 - 0 - 1 2 - 8 1 0 1 5 8 - 2

eBook ISBN:

9 7 8 - 0 - 1 2 - 8 0 0 5 9 0 - 3

Green Synthetic Approaches for Biologically Relevant Heterocycles reviews this significant group of organic compounds within the context of sustainable methods and processes. Each… Read more

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Green Synthetic Approaches for Biologically Relevant Heterocycles reviews this significant group of organic compounds within the context of sustainable methods and processes. Each clearly structured chapter features in-depth coverage of various green protocols for the synthesis of a wide variety of bioactive heterocycles classified on the basis of ring-size and/or presence of heteratoms(s). Techniques covered include microwave heating, ultrasound, ionic liquids, solid phase, solvent-free, heterogeneous catalysis, and aqueous media, along with multi-component reaction strategies. This book also integrates advances in green chemistry research into industrial applications and process developments. Green Synthetic Approaches for Biologically Relevant Heterocycles is an essential resource on green chemistry technologies for academic researchers, R&D professionals, and students working in medicinal, organic, natural product, and agricultural chemistry.

Dedication
About the Editor
Foreword
Preface
Chapter 1. Green Synthetic Approaches for Biologically Relevant Heterocycles: An Overview
- 1. Introduction
- 2. An Overview of the Book
- 3. Concluding Remarks
Chapter 2. Synthesis of Bioactive Five- and Six-Membered Heterocycles Catalyzed by Heterogeneous Supported Metals
- 1. Introduction
- 2. Synthesis of N-Containing Heterocycles
- 3. Synthesis of Oxygen-Containing Heterocycles
- 4. Synthesis of Sulfur-Containing Heterocycles
- 5. Concluding Remarks
Chapter 3. Transition-Metal-Free Synthesis of Benzo-Fused Five- and Six-Membered Heterocycles Employing Arynes
- 1. Introduction
- 2. Synthesis of Five-Membered Heterocycles
- 3. Synthesis of Six-Membered Heterocycles
- 4. Synthesis of Medium-Sized Heterocycles
- 5. Applications of the Benzo-Fused Heterocycles
- 6. Concluding Remarks
Chapter 4. Metal-Catalyzed Routes for the Synthesis of Furocoumarins and Coumestans
- 1. Introduction
- 2. Synthetic Routes to Furocoumarin Derivatives
- 3. Synthetic Routes to Coumestan Derivatives
- 4. Concluding Remarks
Chapter 5. Green Solvents for Eco-friendly Synthesis of Bioactive Heterocyclic Compounds
- 1. Introduction
- 2. Heterocyclic Synthesis in Supercritical Carbon Dioxide
- 3. Heterocyclic Synthesis in PEG
- 4. Heterocyclic Synthesis in Glycerol
- 5. Heterocyclic Synthesis in Gluconic Acid Aqueous Solution
- 6. Heterocyclic Synthesis in Ethyl Lactate
- 7. Concluding Remarks
Chapter 6. Green Catalytic Synthesis of Heterocyclic Structures Using Carbon Dioxide and Related Motifs
- 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
Chapter 7. Synthetic Approaches to Small- and Medium-Size Aza-Heterocycles in Aqueous Media
- 1. Introduction
- 2. Three-Membered Ring—Aziridines
- 3. Four-Membered Rings
- 4. Five-Membered Rings
- 5. Six-Membered Rings
- 6. Seven-Membered Rings
- 7. Concluding Remarks
Chapter 8. Green Synthetic Approaches for Biologically Relevant 2-amino-4H-pyrans and 2-amino-4H-pyran-Annulated Heterocycles in Aqueous Media
- 1. Introduction
- 2. Synthetic Approaches for 2-amino-4H-pyrans and 2-amino-4H-pyran-Annulated Heterocycles in Water and Ethanol–Water Media
- 3. Concluding Remarks
Chapter 9. Sustainable Synthesis of Benzimidazoles, Quinoxalines, and Congeners
- 1. Introduction
- 2. Methods of Synthesis of Benzimidazoles/Quinoxalines Using Greener Strategies
- 3. Concluding Remarks
Chapter 10. Green and Catalytic Methods for γ-Lactone Synthesis
- 1. Introduction
- 2. Constructive Methods for γ-Lactone Structure
- 3. Functionalization of γ-Lactone Structures
- 4. Concluding Remarks
Chapter 11. Green Synthetic Approaches for Medium Ring-Sized Heterocycles of Biological Interest
- 1. Introduction
- 2. Microwave- and Ultrasound-Assisted Synthesis of Medium Ring-Sized Heterocycles
- 3. Use of Ionic Liquids as Reaction Medium and Catalyst
- 4. Use of Environmentally Benign Solvents
- 5. Use of Heterogeneous Catalysis
- 6. Fluorous Synthesis
- 7. Concluding Remarks
Chapter 12. Organocatalyzed Biginelli Reactions: A Greener Chemical Approach for the Synthesis of Biologically Active 3,4-Dihydropyrimidin-2(1H)-ones/-thiones
- 1. Introduction
- 2. Classes of Organocatalysts Used in the Biginelli Reaction
- 3. Biological Significance of 3,4-Dihydropyrimidin-2(1H)-ones/-thiones
- 4. Concluding Remarks
- Abbreviations
Chapter 13. Photocatalytic Minisci Reaction: A Promising and Eco-friendly Route to Functionalize Heteroaromatics of Biological Interest
- 1. Introduction
- 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 Solution?
- 7. Concluding Remarks
Chapter 14. Organohypervalent Iodine Reagents in the Synthesis of Bioactive Heterocycles
- 1. Introduction
- 2. Organohypervalent Iodine Promoted Synthesis of Bioactive Heterocycles
- 3. Concluding Remarks
- Abbreviations
Chapter 15. Porous Catalytic Systems in the Synthesis of Bioactive Heterocycles and Related Compounds
- 1. Introduction
- 2. Porous Catalytic Systems
- 3. Synthesis of Bioactive Heterocycles Catalyzed by Porous Materials
- 4. Concluding Remarks
Chapter 16. High-Pressure Cycloaddition Reactions in the Synthesis of Biologically Relevant Heterocycles
- 1. Introduction
- 2. Diels–Alder Cycloadditions
- 3. Dipolar Cycloadditions
- 4. [2 + 2] Cycloadditions
- 5. Concluding RemarKS
- Abbreviations
Chapter 17. Ionic Liquids-Prompted Synthesis of Biologically Relevant Five- and Six-Membered Heterocyclic Skeletons: An Update
- 1. Introduction
- 2. Properties of ILs
- 3. Recent Developments in Ionic Liquids Research
- 4. Application of Ionic Liquids in Heterocyclic Synthesis
- 5. Concluding Remarks
Chapter 18. Heterocycles-Based Ionic Liquid-Supported Synthesis of Small Organic Molecules
- 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
Chapter 19. Microwave-Induced Synthesis of Heterocycles of Medicinal Interests
- 1. Introduction
- 2. Microwave Irradiation: Mechanism
- 3. Microwave-Induced Synthesis of Heterocycles of Medicinal Interests
- 4. Concluding Remarks
- Abbreviations
Chapter 20. Application of Microwave Irradiation in the Synthesis of P-Heterocycles
- 1. Introduction
- 2. Functionalization of Cyclic Phosphinic Acids
- 3. Diels–Alder Cycloadditions, Fragmentation-Related Phosphorylations, and Inverse Wittig-Type Reactions
- 4. Phospha-Michael Reactions
- 5. Kabachnik–Fields Reactions
- 6. Concluding Remarks
Chapter 21. Use of Ultrasound in the Synthesis of Heterocycles of Medicinal Interest
- 1. Introduction
- 2. Heterocycles of Medicinal Interest
- 3. Concluding Remarks
Index

Goutam Brahmachari

Born on April 14, 1969 in Barala, a village in the district of Murshidabad (West Bengal, India), Goutam Brahmachari had his early education in his native place. He received his high school degree in scientific studies in 1986 at Barala R. D. Sen High School under the West Bengal Council of Higher Secondary Education (WBCHSE). Then he moved to Visva-Bharati (a Central University founded by Rabindranath Tagore at Santiniketan, West Bengal, India) to study chemistry at the undergraduate level. After graduating from this university in 1990, he completed his master’s in 1992 with a specialization in organic chemistry. After that, receiving his Ph.D. in 1997 in chemistry from the same university, he joined his alma mater the very next year and currently holds the position of a full professor of chemistry since 2011. The research interests of Prof. Brahmachari’s group include natural products chemistry, synthetic organic chemistry, green chemistry, and the medicinal chemistry of natural and natural product-inspired synthetic molecules. With about 23 years of experience in teaching and research, he has produced 235 scientific publications, including original research papers, review articles, books, and invited book chapters in the field of natural products and green chemistry. He has already authored/edited 26 books published by internationally reputed major publishing houses, namely, Elsevier Science (The Netherlands), Academic Press (Oxford), Wiley-VCH (Germany), Alpha Science International (Oxford), De Gruyter (Germany), World Scientific (Singapore), CRC Press (Taylor & Francis Group, USA), Royal Society of Chemistry (Cambridge), etc. Prof. Brahmachari serves as a life member for the Indian Association for the Cultivation of Science (IACS), Indian Science Congress Association (ISCA), Kolkata, and Chemical Research Society of India (CRSI), Bangalore. He has also been serving as an associate editor for Current Green Chemistry. Prof. Brahmachari serves as the founder series editor of Elsevier Book Series’ Natural Product Drug Discovery. He is an elected fellow of the Royal Society of Chemistry, and a recipient of CRSI (Chemical Research Society of India) Bronze Medal, 2021 (contributions to research in chemistry), INSA (Indian National Science Academy) Teachers Award, 2019, Dr. Kalam Best Teaching Faculty Award, 2017, and Academic Brilliance Award, 2015 (Excellence in Research). Prof. Brahmachari was featured in the World’s Top 2% Scientists (organic chemistry category) in 2020 and 2021 and the AD Scientific Index 2022 World Ranking of Scientists, 2022.

Affiliations and expertise

Goutam Brahmachari, PhD Full Professor, Organic Chemistry, Department of Chemistry, Visva-Bharati (a Central University), Santiniketan, West Bengal, India