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Amino Group Chemistry

Alfredo Ricci

Hardcover, 408 Pages
First Edition, 2008
ISBN: 978-3-527-31741-7


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.

Editorial Review

Alfredo Ricci and the authors who have contributed to the book "Amino Group Chemistry" have succeeded in bringing together some interesting chapters on the chemistry of the amino group. Synthesis options are highlighted at the outset, while later chapters specifically take a look at the synthesis of natural products and amino analogs, and their significance as drugs.

The chapters are current and contain a number of valuable alternatives to the best-known strategies for the introduction of amino groups. In particular, the published, specific synthesis procedures provided in the first chapter set it apart from the later chapters. Although the Gabriel Synthesis is not described, a surprisingly large number of alternative reagents are covered. Numerous aspects of electrophilic amination are also highlighted. Other chapters are cutting-edge and offer many valuable ideas, for example on the use of nitrenes for C-H amination. Even multi-step strategies are discussed, e.g., for nitro compounds, or using propargylamines as building blocks. With some reservations, these more synthesis-related chapters are very successful. The reservations are that, on the one hand, the high standard set by the first chapter does not necessarily extend into the subsequent chapters, and on the other, because little or no mention is made of some of the general strategies such as reductive amination, Chan-Lam Coupling or the Petasis Reaction. At the same time, the reader gains insights into the construction of complicated compounds via the application of multicomponent reactions or the use of organocatalysts for the construction of chiral compounds, which broaden the horizon considerably.

Chapters 7 and 8 delve in detail into amino sugars, their synthesis and significance as drugs. The chapters have very little overlap and make worthwhile reading, since they exemplify the synthetic strategies through application to specific drug structures. One could envision a chapter dedicated to additional nitrogen-containing natural products, instead of being limited to a specialized field. However, the thematic focus makes a better in-depth treatment possible.

"Amino Group Chemistry" contains a number of chapters that make worthwhile reading, with concrete ideas for the construction of amines and their derivatives. The authors have managed to provide a current overview of selected topics. Chapters 1,2,3,4 and 9 contain a multitude of concrete strategies for preparing simple molecules, whereas the other chapters are devoted to specialized topics in a very readable fashion, all of which tends to round out the book.


1 Simple Molecules, Highly Efficient Amination (Shunsuke 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 Nitrenes (Philippe 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 Tools (Roberto Ballini, 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 Compounds (Alexander 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 Surroundings (Armando 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 Biomolecules (André 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 Activity (Francesco Nicotra, 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 Antivirals (Floris 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 Approach (Ulrich 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.
9.4 Copper-Catalyzed Processes – More Recent Developments.
9.5 Palladium-Catalyzed Processes.
9.6 Nickel-Catalyzed Processes.
9.7 Summary.