Isolated Pyranones

Multifaceted Building Blocks for Molecular Diversity

1st Edition - April 27, 2022
Authors: Vishnu Ji Ram, Atul Goel, Ramendra Pratap
Language: English
Paperback ISBN:
9 7 8 - 0 - 1 2 - 8 2 1 2 1 6 - 5
eBook ISBN:
9 7 8 - 0 - 1 2 - 8 2 3 2 1 2 - 5

Isolated Pyranones: Multifaceted Building Blocks for Molecular Diversity covers the latest findings on synthesis and chemical reactivity of highly functionalized pyran-… Read more

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Isolated Pyranones: Multifaceted Building Blocks for Molecular Diversity covers the latest findings on synthesis and chemical reactivity of highly functionalized pyran-2-ones and pyran-4-ones, their reduced analogs and compounds derived from them through chemical reactions, and their applications in drug discovery and material sciences. It covers the mechanisms of the reaction and step by step formation of final products. Numerous pyranones from natural and synthetic origins, as well as their derived products, have shown diverse pharmacological activities and some are in clinical use. The applications of these compounds are not limited to drug development and imaging agents, and they are also used in material science as organic semiconductors, liquid crystals, organic light emitting diodes (OLEDs), organic catalysts, solid state lasers, photovoltaic and photoconductive devices. The book is ideal for organic, bioorganic, physical, material and natural product chemists working to generate diverse molecular entities through ring transformation reactions of pyranones, and those working in material science to generate new chemical entities.

Cover image
Title page
Table of Contents
Copyright
Preface
Chapter 1. Introduction
Abstract
References
Chapter 2. Characteristics of pyranones
Abstract
References
Chapter 3. Chemistry of isolated 2-pyranones
Abstract
Subchapter 3.1. 2H-Pyran-2-one
3.1.1 Introduction
3.1.2 Characteristics of 2-pyranones
3.1.3 Synthesis of 2H-pyran-2-ones
3.1.4 Reactivity of 2H-pyran-2-ones
3.1.5 Electrophilic addition and substitution reaction
3.1.6 C-Nucleophile-induced ring transformations
3.1.7 Synthesis of 1,2-diaryl-, 1,2,3-triaryl-, 1,2,4-triaryl-, and 1,2,3,4-tetraarylbenzenes
3.1.8 Synthesis of fused compounds
3.1.9 Synthesis of functionalized benzaldehyde and 2-tetralones
3.1.10 Synthesis of metallocenes
3.1.11 Nitrogen nucleophile-induced reactions
3.1.12 Reaction with ammonia source, hydrazine, hydroxylamines, and different amines
3.1.13 Reaction with guanidines
3.1.14 Reaction with amidines
3.1.15 Reaction with benzamides
3.1.16 Reaction with oxoketene cyclic aminals
3.1.17 S-nucleophile-induced ring transformation reactions
3.1.18 Miscellaneous reactions
3.1.19 Reduction
3.1.20 Photochemical reactions
3.1.21 Cycloaddition reactions
3.1.22 Miscellaneous reaction
3.1.23 Conclusion
Subchapter 3.2. Dihydro 2H-pyran-2-ones
3.2.1 3,4-Dihydro-2H-pyran-2-one
3.2.2 Chemical reactivity
3.2.3 Synthetic methodologies
3.2.4 Physical and chemical characteristics
3.2.5 Chemical reactivity
3.2.6 3,6-Dihydro-2H-pyran-2-ones
3.2.7 Synthesis of 3,6-dihydro-2H-pyran-2-ones
3.2.8 Chemical reactivity
3.2.9 Tetrahydro-2H-pyran-2-ones
3.2.10 Chemical characteristics
Subchapter 3.3. Natural isolated pyranones and their medicinal significance
3.3.1 Bufadienolides
3.3.2 Styryl-2-pyranones
3.3.3 4-Hydroxy-2-pyranones
3.3.4 6-Alkyl/alkenyl/aryl-2-pyranones
3.3.5 Neoaureothin, aureothin, luteoreticulin, orinocin
3.3.6 Citreoviridin and derivatives
3.3.7 Asteltoxin and citreomontanin
3.3.8 Wailupemycins and mutacins
3.3.9 Stizolobic acid and stizolobinic acid
Chapter 4. Chemistry of 2H-pyran-3 (6H)-one and dihydro-2H-pyran-3 (4H)-one
Abstract
4.1 Chemistry of 2H-pyran-3(6H)-one (2,6-dihydopyran-3-one)
4.2 Chemistry of dihydro-2H-pyran-3(4H)-one (Tetrahydropyran-3-one)
References
Chapter 5. Chemistry of isolated 4-pyranones
Abstract
5.1 4H-Pyran-4-one (γ-pyranone)
5.2 Biologically active natural products with 4-pyrone moiety
5.3 Chemical reactivity
5.4 2,3-Dihydro-4H-pyran-4-one (2,3-dihydro-4-pyranone)
5.5 4H-Tetrahydropyran-4-one(tetrahydropyran-4-one)
References
Chapter 6. Medicinal significance of natural and synthetic pyranones
Abstract
6.1 Antimicrobial activity
6.2 Cardiovascular disorders
6.3 Antioxidant activity
6.4 Anti-osteoporosis agents
6.5 Antitubercular agent
6.6 Antidiabetic agents
6.7 Pyranone derived fluorescent probes for biomedical applications
References
Chapter 7. Application of pyranones in material sciences
Abstract
7.1 Pyranone-derived π-conjugated systems
References
Chapter 8. Conclusion
Abstract
Abbreviations
Index

Vishnu Ji Ram

Further to his superannuation as Dy. Director for the Central Drug Research Institute, Lucknow, UP, India, a world class, premier research Institute for drug development, Prof Ram became Emeritus professor and served various academic institutions for 10 years. Besides research experience, he has also earned 18 years of experience teaching heterocyclic chemistry to graduate and post-graduate classes. He has 256 publications to his name, including several review articles published in top chemistry journals. He is also recipient of prestigious fellowships from JSPS, Japan, Alexander von Humboldt (AvH), Germany and NIH, USA.

Affiliations and expertise

Emeritus Professor, Lucknow University; former Deputy Director, Central Drug Research Institute, Lucknow, India

Ramendra Pratap

Prof. Ramendra Pratap completed his master’s from the University of Gorakhpur in 2001 and then he moved to Central Drug Research Institute, Lucknow for doctoral research. He worked with Dr. Vishnu Ji Ram for four and a half years on ring transformation reactions of 2H-pyran-2-ones. He worked on nucleoside modification chemistry as a postdoctoral fellow at the City University of New York, USA, for two years. He received a renowned Humboldt fellowship and shifted to the University of Saarland, Germany. In Saarbrucken, he was involved in Mo-catalyzed reactions. In September 2010, He joined the Department of Chemistry, University of Delhi as an Assistant Professor. Currently, He is working as a full Professor. Till now he has published more than 100 research papers in various international Journals. He also received JSPS invitation fellowship during the year 2016-17. His chemistry focuses on developing various heterocycles, carbocycles, materials, and metal-catalyzed bond formation reactions. His major research contribution involves use of isolated and fused pyranones to establish new molecular entities.

Affiliations and expertise

Assistant Professor, Department of Chemistry, Delhi University, India