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Indoles continue to be of great interest to the pharmaceutical industry and at the current time several thousand specific new derivatives are reported annually. Research has been driven by the wide range of indole derivatives which occur in nature and through the biological activity of many indole derivatives, of both natural and synthetic origin.This book provides a systematic guide to the most useful and important reactions in the field for both synthesis and synthetic modification of the indole ring. While including the most recently developed and promising methods, it also updates informationavailable on classical methods to give the reader an up-to-date and comprehensive view of the subject. The methods are illustrated by procedures drawn from the literature and by tables including examples chosen to indicate both the scope of applicabilityand variations in methodology. The organization of the book is based on the retrosynthetic concept of identifying the bond(s) formed in the reaction, which in turn identifies potential starting materials. Includes systematic summaries of the most important methods for the construction of indoles from aromatic precursors Discusses methods for preparing indoles by annelation of pyrroles Covers methods for adding or modifying substituent groups, including methods for introducing the tryptamine and tryptophan side-chainsExamines reduction/oxidation reactions that are specific for indoles Considers use of cycloaddition reactions for synthetic elaboration of indoles
Of the myriad of heterocycles known to man, the indole ring stands foremost for its remarkably versatile chemistry, its enormous range of biological activities, and its ubiquity in the terrestrial and marine environments. The indole ring continues to be discovered in natural products and to be employed in man-made pharmaceuticals and other materials. Given the enormous resurgence in indole ring synthesis over the past decade — highlighted by the power of transition metal catalysis — this authoritative guide addresses the need for a comprehensive presentation of the myriad of methods for constructing the indole ring, from the ancient to the modern, and from the obscure to the well-known. Following presentation of the classic indole ring syntheses and many newer methods, coverage continues with indole ring syntheses via pyrroles, indolines, oxindoles, isatins, radical and photochemical reactions, aryne cycloadditions. This extensive volume concludes with the modern transition metal–catalyzed indole ring syntheses that utilize copper, palladium, rhodium, gold, ruthenium, platinum, and other metals to fashion the indole ring Indole Ring Synthesis is a comprehensive, authoritative and up-to-date guide to the synthesis of this important heterocycle for organic chemists, pharmaceutical researchers and those interested in the chemistry of natural products.
Organic Chemistry, Volume 18: The Chemistry of Indoles discusses the chemistry of indole derivatives. This book explores the potent biological activity of several indole derivatives and explains the structure of indole alkaloids. Organized into 10 chapters, this monograph starts with an overview of the most important types of reactions of the indole ring on a mechanical basis. This text then proceeds to review the methods of synthesizing indoles and describes the oxidations and rearrangements of indole derivatives. Other chapters explore the special features of the synthesis and reactivity of hydroxyindoles, acylindoles, and aminoindoles. This book discusses as well the properties of carboxyl groups, which is substituted on the benzenoid ring of the indole nucleus that is typical of aromatic carboxylic acids. The final chapter deals with the certain classes of indoles that are found in nature. Chemists, researchers, and readers interested in the chemistry of indoles will find this book extremely useful.
This publication sets outs the findings of an IARC Working Group, held in Lyon, France in November 2003, which considered the benefits of a diet rich in cruciferous vegetables in helping to reduce the risk of various cancers. Cruciferous vegetables, such as broccoli, cabbage, cauliflower, watercress and brussel sprouts, contain substantial amounts of compounds which have been shown to inhibit the growth of cancers. This publication reviews current knowledge on the topic, including data from human, experimental and mechanistic studies, as well as making recommendations for future research and public health policy options.
Richard J. Sundberg Electrophilic Substitution Reactions of Indoles Tara L.S. Kishbaugh Reactions of Indole with Nucleophiles Erin Pelkey Metalation of Indole Jie Jack Li ∙ Gordon W. Gribble Metal-Catalyzed Cross-Coupling Reactions for Indoles Jeanese C. Badenock Radical Reactions of Indole Fariborz Firooznia ∙ Robert F. Kester ∙ Steven J. Berthel [2+2], [3+2] and [2+2+2] Cycloaddition Reactions of Indole Derivatives Robert F. Kester ∙ Steven J. Berthel ∙ Fariborz Firooznia [4+2] Cycloaddition Reactions of Indole Derivatives Jonathon S. Russel Oxindoles and Spirocyclic Variations: Strategies for C3 Functionalization Liangfeng Fu Advances in the Total Syntheses of Complex Indole Natural Products
Comprehensive Natural Products III, Third Edition, Seven Volume Set updates and complements the previous two editions, including recent advances in cofactor chemistry, structural diversity of natural products and secondary metabolites, enzymes and enzyme mechanisms and new bioinformatics tools. Natural products research is a dynamic discipline at the intersection of chemistry and biology concerned with isolation, identification, structure elucidation, and chemical characteristics of naturally occurring compounds such as pheromones, carbohydrates, nucleic acids and enzymes. This book reviews the accumulated efforts of chemical and biological research to understand living organisms and their distinctive effects on health and medicine and to stimulate new ideas among the established natural products community. Provides readers with an in-depth review of current natural products research and a critical insight into the future direction of the field Bridges the gap in knowledge by covering developments in the field since the second edition published in 2010 Split into 7 sections on key topics to allow students, researchers and professionals to find relevant information quickly and easily Ensures that the knowledge within is easily understood by and applicable to a large audience
The Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects – properties, synthesis, reactions, physiological and industrial significance – of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.
The Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects – properties, synthesis, reactions, physiological and industrial significance – of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.
The Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects – properties, synthesis, reactions, physiological and industrial significance – of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.
This work investigated a novel photochemical cyclization to form indole derivatives from o-alkynylated F-tagged aniline derivatives, and wide applicability to synthesize differently functionalized indole systems bearing various substituents in the positions N-1, C-2, C-3, C-5 and C-6 was shown. Additionally, this reaction was systematically studied in a kinetic study in an in-house assembled capillary photo-microreactor. Further derivatization of the final F-tagged 3-acylindoles by the cleavage of the perfluorinated chain yielded a library of novel indole-3-carboxylic acid and indole-3-carboxylic acid ester derivatives. A straightforward and efficient four-step methodology for the synthesis of desired indole derivatives with high yields for single steps and the whole sequence was developed. Variing the conditions of single steps showed that all three steps of the reaction route to the cyclization precursors can be performed using the same solvent and base, providing the possibility to conduct this sequence as a continuous-flow without the need for in-line solvent switch or base exchange and without compromises with respect to the selectivity and yields of single steps.