Search results for: indoles

The Chemistry of Indoles

Author : Richard Sundberg
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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.

Indoles Part 4

Author : J. Edwin Saxton
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Internationally renowned specialists present a comprehensive survey of the latest advances in this area. The biosynthetic and structural relationships of these compounds are summarized and newly discovered alkaloids described. Discusses versatile biomimetic procedures as well as the pharmacology and clinical applications of monoterpenoid indole alkaloids. Botanical names of all plants cited have been extensively referenced.

Heterocyclic Scaffolds II

Author : Gordon W. Gribble
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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

Indoles

Author : Richard J. Sundberg
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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

Indoles

Author : Richard J. Sundberg
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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

Indoles Part 4

Author : J. Edwin Saxton
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Internationally renowned specialists present a comprehensive survey of the latest advances in this area. The biosynthetic and structural relationships of these compounds are summarized and newly discovered alkaloids described. Discusses versatile biomimetic procedures as well as the pharmacology and clinical applications of monoterpenoid indole alkaloids. Botanical names of all plants cited have been extensively referenced.

The Preparation of Substituted Indoles from Diazoketones

Author : Charles Ernest Blades
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Cruciferous Vegetables Isothiocyanates and Indoles

Author : International Agency for Research on Cancer
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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.

Indoles

Author : William J. Houlihan
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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.

Novel Methods for the Synthesis of Functionalised Indoles

Author : Karim Aboutayab
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Indole

Author : Bridget Pratt
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In the foremost chapter of Indole: Synthesis, Functions and Reactions, derivatives of hydrogenated pyrido[4,3-b]indoles as potential neuroprotectors have been synthesized. Different substituents were introduced into position 8 of the carboline fragment of the molecule: methyl-, methoxy-, fluorine- and chlorine-ones. Biological tests have shown that all the studied compounds can modulate glutamate-dependent uptake of calcium ions in rats cerebral cortex synaptosomes. The authors go on to discuss how mushrooms and their mycelia from in vitro cultures have become increasingly common study subjects due to their health-promoting potential. The most frequently demonstrated properties of these mushrooms include antioxidative, anticancer, anti-inflammatory, immunostimulatory and anti-depressive effects. This activity stems from numerous mushroom metabolites, bioelements and physiologically active substances, including indole compounds. The final chapter provides an overview of the diverse synthetic approaches to generate pyrimido[4,5-b]indoles. Pyrimido-indoles are tricyclic ring systems produced when an indole group is fused with a pyrimidine ring. Of the two possible isomers of this ring system, the pyrimido[4,5-b]indoles are of particular interest relative to pyrimido[5,4-b]indoles due to their presence in a wide range of pharmacologically active molecules.

Indoles

Author : William J. Houlihan
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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.

Indoles

Author : William J. Houlihan
File Size : 83.96 MB
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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 Indoles

Author : J. Edwin Saxton
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Indole Ring Synthesis

Author : Gordon W. Gribble
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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.

Application of Iridium catalysed C H Borylation to the Functionalisation of Indoles

Author : Andrew Eastabrook
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This thesis describes several novel applications of the iridium-catalysed C–H borylation of indoles. Research commenced with the development of a general procedure for the conversion of indoles 242 to 7-hydroxyindoles 245 and indolequinones 243. This was achieved by a three-step procedure – an initial C7–H borylation was followed by hydrogen peroxide-mediated oxidative hydrolysis affording the 7-hydroxyindoles 245. Upon oxidation with salcomine/O2 these 7-hydroxyindoles 245 were converted to the indolequinones 243. This is the first general procedure that can be used to convert indoles to indolequinones. We developed a general procedure for the triborylation of indoles, and subjected a variety of indoles to this transformation. In the absence of a substituent at C3, the triborylation was directed to C2 and C7 by the indole N–H, followed by a sterically-governed C–H borylation, which gave a mixture of C4–H and C5–H borylated products, favouring the former. In the case of 3-substituted indoles, the sterically-governed C–H borylation was selective for C5–H, affording 2,3,5,7-tetrasubstituted indoles 246. A selection of these triborylated indoles were synthesised, demonstrating that this procedure is general and can be used to selectively functionalise three C–H bonds in a single operation. We subsequently developed several new applications of the aforementioned C–H triborylation. A one-pot triborylation-protodeborylation procedure delivered 5,7- diborylindoles 500. Further functionalisation of these 5,7-diborylindoles 500 enabled access to rare 3,5,7-trisubstituted indoles 247, such as the natural product plakohypaphorine C 536 and those that are differentially substituted at C5 and C7. Finally, we developed a novel indole to benzoxazole rearrangement enabled by C–H borylation. 2,3-Dimethylindole 349 was converted to the 7-borylindole 350. Upon treatment with mCPBA under basic conditions, concomitant oxidative hydrolysis of the arylboronate and oxidative cleavage of the indole C2–C3 bond occurred, giving the amidophenol 581. Cyclisation to give the benzoxazole 582 was achieved with TFA.

Monoterpenoid Indole Alkaloids Supplement to Part 4

Author : J. Edwin Saxton
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Internationally renowned specialists present a comprehensive survey of the latest advances in this area. The biosynthetic and structural relationships of these compounds are summarized and newly discovered alkaloids described. Discusses versatile biomimetic procedures as well as the pharmacology and clinical applications of monoterpenoid indole alkaloids. Botanical names of all plants cited have been extensively referenced.

Regioselective Iridium Catalyzed C H Activation borylation of 2 substituted Indoles

Author : Sulagna Paul
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Design and Synthesis of New Ligands and Heterocycles from Activated Indoles

Author : Karin Pchalek
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Some Aspects of the Chemistry of Indoles and Indole Alkaloids

Author : B. Robinson
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