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.
The series Topics in Organometallic Chemistry presents critical overviews of research results in organometallic chemistry. As our understanding of organometallic structure, properties and mechanisms increases, new ways are opened for the design of organometallic compounds and reactions tailored to the needs of such diverse areas as organic synthesis, medical research, biology and materials science. Thus the scope of coverage includes a broad range of topics of pure and applied organometallic chemistry, where new breakthroughs are being achieved that are of significance to a larger scientific audience. The individual volumes of Topics in Organometallic Chemistry are thematic. Review articles are generally invited by the volume editors. All chapters from Topics in Organometallic Chemistry are published OnlineFirst with an individual DOI. In references, Topics in Organometallic Chemistry is abbreviated as Top Organomet Chem and cited as a journal.
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.
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. - Considered the definitive serial in the field of heterocyclic chemistry - Serves as the go-to reference for organic chemists, polymer chemists and many biological scientists - Provides the latest comprehensive reviews written by established authorities in the field - Combines descriptive synthetic chemistry and mechanistic insight to enhance understanding of how chemistry drives the preparation and useful properties of heterocyclic compounds
This volume is devoted to compounds in which the spiro centre is part of a pyranoid or furanoid or an iminosugar ring. The chapters contributed deal with methodological peculiarities of syntheses of natural and artificial sugar derived spirocycles as well as their biological applications and other utilities including marketed drugs. Carbohydrates are ubiquitous molecules in nature and participate in a vast number of biological interactions. Especially their conjugates with practically all kinds of primary and secondary metabolic small molecules (and also biomacromolecules) representing valuable tools for glycobiology research and also lead compounds for drug discovery. While monosaccharides per se appear as heterocycles, their natural conjugates frequently exhibit spiro(hetero)cyclic derivatives, in many cases of high therapeutical relevance. As a consequence, the field of carbohydrate-spiro-heterocycles attracts intense interest from both chemical and biomedical aspects therefore this volume will be of interest for synthetic and medicinal chemists and (glyco)biologists, as well as researchers involved in various biomedical fields.
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.
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.
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.
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.
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.
