Cover image for Amino group chemistry : from synthesis to the life sciences
Title:
Amino group chemistry : from synthesis to the life sciences
Publication Information:
Weinheim : Wiley-VCH, 2008
ISBN:
9783527317417
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30000010161124 QD431 A444 2008 Open Access Book Book
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Summary

Summary

Here, probably the most important functional group in organic chemistry is discussed in one handy volume. The monograph covers its application -- from natural products to synthetic pharmaceuticals -- detailing complex syntheses using the amino group as templates and modern techniques focussing on the introduction of the amino group. A definitive must-have for every chemist.


Author Notes

Alfredo Ricci is full professor in Organic Chemistry at the Chemistry Department of the Faculty of Industrial Chemistry (Bologna University). He was appointed in Florence where he spent part of his career covering for many years the roles of Department head and Director of the National Research Council. 1990 he moved to the University of Bologna. Professor Ricci has authored more than 250 scientific publications and received several scientific awards, including the 2000 French-Italian Prize for Synthetic Organic Chemistry and in 2005 the "A. Mangini" Gold Medal. Since 1995 he is member of the 'Honorary Advisory Board' of Synlett and in 2000 served as editor of the Wiley-VCH book "Modern Amination Methods".


Reviews 1

Choice Review

Amino compounds are the synthetic targets of many pharmaceutical, natural product, and materials chemists. This useful compilation comprises nine chapters that approach amino group synthesis from multiple perspectives. Three well-written chapters feature the synthesis of nitrogen-based biomolecules. Highlighted in these chapters are aminated sugars and aminoglycoside derivatives, leading to an in-depth discussion of antiviral and antibiotic syntheses. Modern and useful chapters detail direct amination methods and include representative procedures and extensive references. Multicomponent isocyanate reactions, asymmetric Mannich reactions, and nitroalkene reactions receive separate, extensive attention, with stereochemistry considered when possible. A chapter on transition metal-catalyzed amination reactions includes recent information on ligand and catalyst selection. An interested reader or student will rapidly gain insight into approaches to amino groups, while a chemist pursuing synthetic work on these challenging compounds will find numerous examples, procedures, and citations to the primary literature. Summing Up: Recommended. Academic and professional chemistry libraries, all levels. I. J. Rhile Albright College


Table of Contents

Preface
List of Contributors
1 Simple Molecules, Highly Effi cient AminationShunsuke Chiba and Koichi Narasaka
1.1 Introduction
1.2 Hydroxylamine Derivatives
1.3 Oxime Derivatives
1.4 Azo Compounds
1.5 Oxaziridine Derivatives
1.6 Chloramine-T
1.7 N-Sulfonyliminophenyliodinane
1.8 Transition Metal-Nitride Complexes
1.9 Azido Derivatives
1.10 Gabriel-Type Reagents
1.11 Conclusion
2 Catalytic C-H Amination with NitrenesPhilippe Dauban and Robert H. Dodd
2.1 Introduction
2.2 Historical Overview
2.3 Hypervalent Iodine-Mediated C−H Amination
2.4 Other Nitrene Precursors for C−H Amination
2.5 Amination of Aromatic C−H Bonds
2.6 Applications in Total Synthesis
2.7 Conclusions
3 Nitroalkenes as Amination ToolsRoberto Ballini and Enrico Marcantoni and Marino Petrini
3.1 Introduction
3.2 General Strategies for the Synthesis of Nitroalkenes
3.3 Synthesis of Alkylamines
3.4 Pyrrolidine Derivatives
3.5 Piperidines and Piperazines
3.6 Pyrrolizidines and Related Derivatives
3.7 Arene-Fused Nitrogen Heterocycles
3.8 Other Polycyclic Derivatives
3.9 Conclusion
4 Isocyanide-Based Multicomponent Reactions (IMCRs) as a Valuable Tool with which to Synthesize Nitrogen-Containing CompoundsAlexander Doemling
4.1 Introduction
4.2 The Ugi Reaction
4.3 Passerini Reaction
4.4 van Leusen Reaction
4.5 Other IMCRs
4.6 Outlook
5 Direct Catalytic Asymmetric Mannich Reactions and SurroundingsArmando Córdova and Ramon Rios
5.1 Introduction
5.2 Organometallic Catalysts
5.3 Metal-Free Organocatalysis
5.4 Conclusions
6 Amino-Based Building Blocks for the Construction of BiomoleculesAndré Mann
6.1 Introduction
6.2 Propargylamines (PLAs)
6.3 trans-4-Hydroxy-(S)-proline (HYP)
6.4 L-Serine (SER)
6.5 4-Methoxypyridine (MOP)
6.6 Aziridines (AZIs)
6.7 Homoallylamine (HAM)
6.8 Indole (IND)
6.9 Conclusion
7 Aminated Sugars, Synthesis, and Biological ActivityFrancesco Nicotra and Barbara La Ferla and Cristina Airoldi
7.1 Biological Relevance of Aminated Sugars
7.2 Synthesis of Aminated Sugars
7.3 Synthesis of Iminosugars
7.4 Conclusions
8 Selective N-Derivatization of Aminoglycosides en Route to New Antibiotics and AntiviralsFloris Louis van Delft
8.1 Aminoglycoside Antibiotics
8.2 RNA Targeting by Aminoglycosides
8.3 The Role of Amino Functions in RNA Binding
8.4 Development of RNA-Targeting Drugs
8.5 Concluding Remarks
9 Evolution of Transition Metal-Catalyzed Amination Reactions: the Industrial ApproachUlrich Scholz
9.1 Introduction: First Steps in the Field of Catalytic Aromatic Amination
9.2 Alternatives to Transition Metal-Catalyzed Arylamination
9.3 The Quest for Industrial Applications of Transition Metal-Catalyzed Arylamination
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