Free-Radical Synthesis and Functionalization of Heterocycles

Free-Radical Synthesis and Functionalization of Heterocycles PDF Author: Yannick Landais
Publisher: Springer
ISBN: 3319895214
Category : Science
Languages : en
Pages : 356

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Book Description
This volume describes the recent developments in the free-radical mediated synthesis and elaboration of heterocycles. The first chapter, dealing with radical cascade processes illustrates the power and the beauty of radical chemistry with some striking examples of total synthesis of complex natural heterocycles. As organic chemists strive towards sustainability, radical chemistry has recently seen major advances and efforts in this direction, including C-H activation of arenes and unactivated alkyl groups. Photochemical activation, for a long time the preferred mode of activation in radical chemistry has also seen an unexpected revival with the advent of visible light metal- and organocatalyzed photoredox processes. A survey of these emerging areas is provided along with the concepts at the origin of these developments. The venerable Minisci reaction allows for direct access to functionalized heterocycles. This process has lately seen an interesting renaissance and is discussed in this volume. Addition of heteroatom-centered radicals onto unsaturated systems constitutes another powerful method to construct heterocycles. Examples of such a strategy are proposed along with the formation of various heterocycles relying on homolytic substitution at sulfur, phosphorus and selenium. Additionally free-radical functionalization of reactive functional groups including isonitriles, isothiocyanates and related unsaturated systems which offer a straightforward route towards useful aromatic and non-aromatic heterocycles are discussed. Finally, as metals are able to trigger single electron transfer both in reductive and oxidative modes this provides another possibility for the synthesis of heterocycles. Significant research efforts have focused on the use of samarium, copper and other metals to access a broad variety of heterocycles in a single pot process, starting from readily available raw material. Examples and mechanistic insights are discussed by experts in this area.

Free-Radical Synthesis and Functionalization of Heterocycles

Free-Radical Synthesis and Functionalization of Heterocycles PDF Author: Yannick Landais
Publisher: Springer
ISBN: 3319895214
Category : Science
Languages : en
Pages : 356

Get Book Here

Book Description
This volume describes the recent developments in the free-radical mediated synthesis and elaboration of heterocycles. The first chapter, dealing with radical cascade processes illustrates the power and the beauty of radical chemistry with some striking examples of total synthesis of complex natural heterocycles. As organic chemists strive towards sustainability, radical chemistry has recently seen major advances and efforts in this direction, including C-H activation of arenes and unactivated alkyl groups. Photochemical activation, for a long time the preferred mode of activation in radical chemistry has also seen an unexpected revival with the advent of visible light metal- and organocatalyzed photoredox processes. A survey of these emerging areas is provided along with the concepts at the origin of these developments. The venerable Minisci reaction allows for direct access to functionalized heterocycles. This process has lately seen an interesting renaissance and is discussed in this volume. Addition of heteroatom-centered radicals onto unsaturated systems constitutes another powerful method to construct heterocycles. Examples of such a strategy are proposed along with the formation of various heterocycles relying on homolytic substitution at sulfur, phosphorus and selenium. Additionally free-radical functionalization of reactive functional groups including isonitriles, isothiocyanates and related unsaturated systems which offer a straightforward route towards useful aromatic and non-aromatic heterocycles are discussed. Finally, as metals are able to trigger single electron transfer both in reductive and oxidative modes this provides another possibility for the synthesis of heterocycles. Significant research efforts have focused on the use of samarium, copper and other metals to access a broad variety of heterocycles in a single pot process, starting from readily available raw material. Examples and mechanistic insights are discussed by experts in this area.

Heterocycles via Cross Dehydrogenative Coupling

Heterocycles via Cross Dehydrogenative Coupling PDF Author: Ananya Srivastava
Publisher: Springer Nature
ISBN: 9811391440
Category : Science
Languages : en
Pages : 498

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Book Description
This book discusses the developments in the synthesis and functionalization of different heterocycles based on the formation of carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds using cross-dehydrogenative coupling (CDC). Consisting of 13 chapters, the book systematically describes the advances in the synthesis and functionalization of nitrogen, oxygen, and sulfur-containing heterocycles. It also discusses the various mechanistic pathways to help readers gain an in-depth understanding of the CDC reactions of heterocycles. Lastly, in order to promote green chemistry, it addresses a range of metal-free CDC reactions of heterocycles – an area that has attracted significant attention in both academic and industrial research.

Multicomponent Reactions towards Heterocycles

Multicomponent Reactions towards Heterocycles PDF Author: Erik Van der Eycken
Publisher: John Wiley & Sons
ISBN: 3527349081
Category : Science
Languages : en
Pages : 626

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Book Description
Presents a wide-ranging overview of essential topics and recent advances in MCR chemistry Heterocycles are a central component in natural product chemistry, pharmaceuticals, agrochemicals, and material science. New synthetic methodologies integrating the sequencing of multicomponent reactions (MCRs) are today being used for the rapid synthesis of diversified heterocycles in just one step. Multicomponent Reactions towards Heterocycles presents an up-to-date summary MCR chemistry with a focus on the conjugation between modern synthetic methodologies and MCRs. Featuring contributions by leaders in the field, this comprehensive resource highlights applications of MCRs in natural products and intermediate synthesis, discusses current trends and future prospects in MCR chemistry, outlines novel multicomponent procedures, and more. The authors provide the practical information required for designing new reaction strategies and mechanisms, covering topics including MCR-based green synthetic methods, cyclization and cycloaddition reactions, heterocycle multicomponent syntheses in a continuous flow, catalytic alkynoyl generation, MCR synthesis of saturated heterocycles, and C–H functionalization and multicomponent reactions. Provides a thorough overview of heterocycles as input in multicomponent reactions Discusses recent advances in the field of MCR chemistry and progress in the synthesis and functionalization of heterocycles Demonstrates the use of MCRs to simplify synthetic design and achieve complexity and diversity in novel bioactive molecules Highlights examples of multicomponent polymerizations, target-oriented synthesis, and applications of MCR in medicinal chemistry Explains the methodology of using on-resin MCRs to produce heterocycle compounds Illustrating the key role of MCRs towards heterocycles in natural product synthesis, drug discovery, organic synthesis, and other applications, Multicomponent Reactions towards Heterocycles is required reading for synthetic chemists in academia and industry alike.

Visible Light Photocatalysis in Organic Chemistry

Visible Light Photocatalysis in Organic Chemistry PDF Author: Corey R.J. Stephenson
Publisher: John Wiley & Sons
ISBN: 3527335609
Category : Science
Languages : en
Pages : 454

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Book Description
Filling the need for a ready reference that reflects the vast developments in this field, this book presents everything from fundamentals, applications, various reaction types, and technical applications. Edited by rising stars in the scientific community, the text focuses solely on visible light photocatalysis in the context of organic chemistry. This primarily entails photoinduced electron transfer and energy transfer chemistry sensitized by polypyridyl complexes, yet also includes the use of organic dyes and heterogeneous catalysts. A valuable resource to the synthetic organic community, polymer and medicinal chemists, as well as industry professionals.

Multicomponent Reactions in Organic Synthesis

Multicomponent Reactions in Organic Synthesis PDF Author: Jieping Zhu
Publisher: John Wiley & Sons
ISBN: 3527332375
Category : Science
Languages : en
Pages : 512

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Book Description
Comprehensive and up-to-date, this book focuses on the latest advances in the field, such as newly developed techniques, more environmentally benign processes, broadened scopes, and completely novel MCRs. In addition to carbene-promoted MCRs and frequently applied metal-catalyzed MCRs, it also covers recently developed catalytic enantioselective variants as well as MCR in drug discovery and for the synthesis of heterocyclic molecules and macrocycles. Edited by the leading experts and with a list of authors reading like a "who's who" in multicomponent reaction chemistry, this is definitely a must-have for every synthetic organic chemist as well as medicinal chemists working in academia and pharmaceutical companies.

Free Radicals in Organic Chemistry

Free Radicals in Organic Chemistry PDF Author: Jacques Fossey
Publisher:
ISBN:
Category : Business & Economics
Languages : en
Pages : 328

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Book Description
Free radicals constitute the most frequently used class of reaction intermediates in organic chemistry. This study describes the structure and reactivity of free radicals, and explores their role in both natural phenomena and in the design of new reaction pathways.

Iodine Catalysis in Organic Synthesis

Iodine Catalysis in Organic Synthesis PDF Author: Kazuaki Ishihara
Publisher: John Wiley & Sons
ISBN: 3527348298
Category : Technology & Engineering
Languages : en
Pages : 452

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Book Description
Iodine Catalysis in Organic Synthesis The first book of its kind to highlight iodine as a sustainable alternative to conventional transition metal catalysis Iodine Catalysis in Organic Synthesis provides detailed coverage of recent advances in iodine chemistry and catalysis, focusing on the utilization of various iodine-containing compounds as oxidative catalysts. Featuring contributions by an international panel of leading research chemists, this authoritative volume explores the development of environmentally benign organic reactions and summarizes catalytic transformations of molecular iodine and iodine compounds such as hypervalent organoiodine and inorganic iodine salts. Readers are first introduced to the history of iodine chemistry, the conceptual background of homogeneous catalysis, and the benefits of iodine catalysis in comparison with transition metals. Next, chapters organized by reaction type examine enantioselective transformations, catalytic reactions involving iodine, catalyst states, oxidation in iodine and iodine catalyses, and catalytic reactions based on halogen bonding. Practical case studies and real-world examples of different applications in organic synthesis and industry are incorporated throughout the text. An invaluable guide for synthetic chemists in both academic and industrial laboratories, Iodine Catalysis in Organic Synthesis: Provides a thorough overview of typical iodine-catalyzed reactions, catalyst systems, structures, and reactivity Explores promising industrial applications of iodine-based reagents for organic synthesis Highlights the advantages iodine catalysis has over classical metal-catalyzed reactions Discusses sustainable and eco-friendly methods in hypervalent iodine chemistry Edited by two world authorities on the catalytic applications of organoiodine compounds, Iodine Catalysis in Organic Synthesis is required reading for catalytic, organic, and organometallic chemists, medicinal and pharmaceutical chemists, industrial chemists, and academic researchers and advanced students in relevant fields.

Amino Acids: Insights and Roles in Heterocyclic Chemistry

Amino Acids: Insights and Roles in Heterocyclic Chemistry PDF Author: Zerong Wang
Publisher: CRC Press
ISBN: 1000751694
Category : Science
Languages : en
Pages : 1675

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Book Description
This first-of-its-kind four-volume book series, Amino Acids: Insights and Roles in Heterocyclic Chemistry, provides readers with up-to-date information on alpha-amino acids, the potential challenges in working with alpha-amino acids, the protecting groups for the carboxyl, amino and side chain groups of the amino acids, and the most popular heterocyclic compounds that are originating from alpha-amino acids. These heterocyclic compounds include hydantoins, thiohydantoins (including 2-thiohydantoins, 4-thiohydantoins, 2,4-dithiohydantoins), 2,5-diketopiperazines, N-carboxyanhydrides, N-thiocarboxyanhydrides, sydnones, sydnonimines, azlactones, pseudoazlactones, and oxazolidin-5-ones. This is the first resource to comprehensively collect all the heterocycles that can be directly prepared from alpha-amino acids. In addition, almost all kinds of synthetic methods for a particular type of heterocycles from alpha-amino acids are included, along with the detailed mechanistic discussions and experimental procedures. Volume 1: Protecting Groups collects and discusses the 260 protecting groups relating to amino acids, which have been organized by carboxyl group, amino group, and side chain groups. The conditions to introduce these protecting groups as well as their deprotecting procedures have also been incorporated, along with the physical properties, solvent effects, and temperature effects on the solubility of amino acids. It presents the solubility of glycine and phenylalanine in a variety of solvent systems to show the impact on amino acid, where glycine generally represents the polar amino acid whereas phenylalanine represents the amino acid of non-polar side chain. In Volume 2: Hydantoins, Thiohydantoins, and 2,5-Diketopiperazines, the author has compiled the three IUPAC accepted nomenclature systems for heterocyclic compounds, which will be very useful for readers working in the heterocyclic chemistry field for giving the synthesized molecules their correct names. In addition, three groups of heterocyclic compounds, i.e., hydantoins, thiohydantoins (including 2-thiohydantoin, 4-thiohydantoin and 2,4-dithiohydantoin), and 2,5-diketopiperazines, have been organized with updated literature information. Particularly, all three groups of heterocyclic compounds have demonstrated many important biological activities, particularly anticancer and antibacterial activities. On the other hand, these three groups of heterocycles can be applied as substrates to make other chemical derivatives, particularly novel unnatural amino acids. All their reactivities have been compiled and updated. These will be very valuable for readers who have been working in this area or have interest in this area. Volume 3: N-Carboxyanhydrides, N-Thiocarboxyanhydrides, and Sydnones presents up-to-date detailed information on two types of heterocyclic compounds that are originated from alpha-amino acids: NCAs/NTAs and sydnones/sydnonimines. The volume also covers the more than 10 initiating systems for the NCA monomers to undergo the ring-opening polymerization, which are very useful for readers in order to make living polypeptides/polypeptoids. In addition, the method to characterize these prepared polypeptides/polypeptoids are included. Particularly, two modern mass spectrometric techniques (MALDI-TOF and ESI-TOF) have been explained with detailed examples, where the elucidation of molecular weight of protein based on the ESI-TOF spectra have been given with a practical example as well as the theory that is based on, a unique feature of the volume. Volume 4: Azlactones and Oxazolidin-5-ones discusses two types of simple heterocycles that can be prepared from alpha-amino acids, i.e., azlactones (also known as oxazolones, 4-unsaturated azlactones included) and oxazolidin-5-ones. These heterocyclic compounds behave differently in both biological and chemical properties, and their biological activities are presented in a well-organized manner in this volume. This unique 4-volume set thoroughly covers more than seven types of heterocyclic compounds that are originated from alpha-amino acids, providing carefully compiled updated information with detailed examples. The author has shared many thoughtful insights based on his strong background in physical organic chemistry. The volumes will be highly valuable for graduate students and senior students, as well as for professors and researchers working in the field of medicinal and pharmaceutical chemistry, organic chemistry, organic synthesis, heterocycles, and proteins and peptides.

Nitroxides

Nitroxides PDF Author: Olivier Ouari
Publisher: Royal Society of Chemistry
ISBN: 1788019660
Category : Science
Languages : en
Pages : 611

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Book Description
Nitroxides are versatile small organic molecules possessing a stabilised free radical. With their unpaired electron spin they display a unique reactivity towards various environmental factors, enabling a diverse range of applications. They have uses as synthetic tools, such as catalysts or building blocks; imaging agents and probes in biomedicine and materials science; for medicinal antioxidant applications; and in energy storage. Polynitroxides (polymers bearing pendant nitroxide sidechains) have been used in organic radical batteries, oxidation catalysts and in exchange reactions for constructing complex architectures. Chapters in this book cover the synthesis of nitroxides, EPR studies and magnetic resonance applications, physiochemical studies, and applications including in batteries, imaging and organic synthesis. With contributions from leaders in the field, Nitroxides will be of interest to graduate students and researchers across chemistry, physics, biology and materials science.

Advances in Heterocyclic Chemistry

Advances in Heterocyclic Chemistry PDF Author:
Publisher: Academic Press
ISBN: 0128211687
Category : Science
Languages : en
Pages : 492

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Book Description
Advances in Heterocyclic Chemistry is the definitive series in the field - one of great importance to organic chemists, polymer chemists, and many biological scientists. Because biology and organic chemistry increasingly intersect, the associated nomenclature also is being used more frequently in explanations. Written by established authorities in the field from around the world, this comprehensive review combines descriptive synthetic chemistry and mechanistic insight to yield an understanding of how chemistry drives the preparation and useful properties of heterocyclic compounds.