More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles, 2 Volume Set

Name: More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles, 2 Volume Set
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Ana Maria Faisca Phillips(Herausgeber*in)

Wiley (Verlag)

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Erschienen am 8. April 2022

752 Seiten

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More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles

An authoritative collection of resources discussing the latest trends in the synthesis of nonaromatic nitrogen heterocycles

Widely distributed in nature, nitrogen heterocycles are extremely common in synthetic substances found in pharmaceuticals, agrochemicals, and materials. The literature is evolving rapidly and explores newly emerging structures and medicines. More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles offers R&D professionals the opportunity to easily access a collection of the latest relevant research in the area.

In the second two-volume set of this practical reference distinguished researcher Dr. Ana Maria M. M. Faisca Phillips delivers a collection of resources focusing on the newest and most widely applicable trends emerging in synthetic strategies for nonaromatic nitrogen heterocycles. With coverage of topics including organocatalysis, cascade reactions, flow chemistry in synthesis, cycloaddition reactions, metathesis, cross-coupling reactions, and electrochemistry, the book provides quick access to critical new avenues of synthesis.

More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles: Volume 1 and 2 also offers readers:

* A thorough introduction to recent advances in the design and synthesis of cyclic peptidomimetics

* Comprehensive explorations of fused heterocycles and transition metal promoted synthesis of isoindoline derivatives

* Practical discussions of 1,4-diazepane ring-based systems and recent advances in the synthesis of azepane-based compounds

* In-depth examinations of strained aziridinium ions, asymmetric organocatalysis in alternative media, and the electrochemical synthesis of non-aromatic N-heterocycles

Perfect for academic and industrial researchers in organic chemistry and synthesis, organometallic chemistry, pharmaceutical chemistry catalysis, and sustainable chemistry, More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles: Volume 1 and 2 is an indispensable reference for anyone seeking an authoritative source of information on new and emerging trends in synthesis.

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Inhalt

Cover
Title Page
Copyright
Contents
List of Contributors
Preface
Part I CASCADE REACTIONS
Chapter 1 Unity is Strength
1.1 Introduction
1.2 Rhodium Promoted Reactions
1.3 Palladium Promoted Reactions
1.4 Ruthenium Promoted Reactions
1.5 Cobalt Promoted Reactions
1.6 Miscellaneous Reactions
References
Chapter 2 Chemo-Enzymatic Cascade Reactions for the Synthesis of Chiral Intermediates and Nonaromatic Nitrogen Heterocycles
2.1 Introduction
2.2 C N Bond Construction Enzymes
2.3 C N Deracemization Enzymes
2.4 Cascade Reactions
2.4.1 Enzymatic Cascade Reactions
2.4.2 Chemoenzymatic Cascade Reactions
References
Chapter 3 Asymmetric Organocatalytic Cascade Reactions for the Synthesis of Nitrogen Heterocycles
3.1 Introduction
3.2 Three-Membered Ring Heterocycles: Aziridines
3.3 Four-Membered Ring Heterocycles: The ß-Lactams
3.4 Five-Membered Rings
3.4.1 Pyrrolidines
3.4.2 Pyrrolidinones (?-Lactams)
3.4.3 Isoindolinones and Spirooxindoles
3.4.3.1 Isoindolinones
3.4.3.2 Spirocyclic Oxindoles
3.5 Six-Membered Rings
3.5.1 Piperidines, Dihydropyridines, and Tetrahydropyridines
3.5.2 Piperidinones (d-Lactams)
3.5.3 Dihydropyridinones
3.5.4 Tetrahydroquinolines, Dihydroquinolines, and Related Substances
3.5.5 Hexahydropyridazines and Pyrimidinones
3.6 Pyrrolo[3,2,1-ij]quinolines
3.7 Cyclic Sulfamidates
3.8 Miscellaneous
3.9 Conclusions
Acknowledgments
References
Part II SELECTED REACTIONS FOR THE SYNTHESIS OF NITROGEN HETEROCYCLES
Chapter 4 Synthesis of Nitrogen-Heterocycles Based on N-Heterocyclic Carbene Organocatalysis
4.1 Introduction
4.2 NHC-Catalyzed Cyclization
4.3 NHC-Catalyzed Annulation
4.3.1 [3?+?2] Annulation
4.3.2 [4?+?2] Annulation
4.3.3 [3?+?3] Annulation
4.3.4 [4?+?3] Annulation
4.3.5 [2?+?2] Annulation
4.4 Oxidative NHC-Catalyzed Annulation
4.4.1 Oxidative [3?+?2] Annulation
4.4.2 Oxidative [4?+?2] Annulation
4.4.3 Oxidative [3?+?3] Annulation
4.4.4 Oxidative [4?+?3] Annulation
4.4.5 Oxidative [2?+?2] Annulation
4.5 Asymmetric Dearomatization
4.6 Cooperative Catalysis of NHC and Transition-Metal Catalysts
4.7 Other NHC-Catalyzed Reactions
4.8 Conclusion and Outlook
References
Chapter 5 Synthesis of N-Heterocycles via [3?+?n] Cycloaddition Reactions of Vinyl Metal Carbene Intermediates
5.1 Introduction
5.2 [3?+?1]-Cycloaddition
5.3 [3?+?2]-Cycloaddition
5.4 [3?+?3]-Cycloaddition
5.4.1 [3?+?3]-Cycloaddition with Nitrones
5.4.2 [3?+?3]-Cycloaddition with Azomethine Imines
5.4.3 [3?+?3]-Cycloaddition with Other 1,3-Dipoles
5.5 [3?+?4]-Cycloaddition
5.5.1 [3?+?4]-Cycloaddition with N-Heterocycles
5.5.2 [3?+?4]-Cycloaddition with a,ß-Unsaturated Imines
5.5.3 Other Types of [3?+?4]-Cycloadditions
5.6 [3?+?5]-Cycloaddition
5.7 Intramolecular Cyclization via Carbene/Alkyne Metathesis Process
5.8 Summary and Outlook
References
Chapter 6 Recent Progress in the Synthesis of Amine-Containing Heterocycles by Metathesis Reactions
6.1 Introduction
6.2 Five-Membered Cyclic Amines
6.3 Six-Membered Cyclic Amines
6.3.1 Natural Products and Related Compounds
6.3.2 Sugar Mimetics
6.3.3 RCM of Phenylamines and Related Analogues
6.3.4 Miscellaneous
6.4 Seven-Membered to Macrocyclic Amines
6.5 Tandem Reactions
6.6 Conclusion
References
Chapter 7 Metal-Catalyzed Synthesis of N-Heterocycles via Borrowing-Hydrogen Annulation
7.1 Introduction
7.2 Metal-Catalyzed Borrowing Hydrogen Annulation Reactions
7.2.1 Rh-Catalyzed Borrowing Hydrogen Reactions
7.2.2 Ru-Catalyzed Borrowing Hydrogen Reactions
7.2.3 Ir-Catalyzed Borrowing Hydrogen Reactions
7.2.4 Fe-Catalyzed Borrowing Hydrogen Reactions
7.2.5 Ni-Catalyzed Borrowing Hydrogen Reactions
7.3 Conclusions
Acknowledgments
References
Chapter 8 Synthesis of N-Heterocycles via Intramolecular Pd-Catalyzed C N Buchwald-Hartwig Reaction
8.1 Introduction
8.2 Applications of Intramolecular Pd-Catalyzed N-Arylation of Amines in the Synthesis of Nonaromatic Heterocycles
8.2.1 Synthesis of Five-Membered N-Heterocycles
8.2.2 Synthesis of Six-Membered N-Heterocycles
8.2.3 Applications in the Synthesis of both Five- and Six-Membered N-Heterocycles
8.2.4 Synthesis of Seven-Membered N-Heterocycles
8.3 Applications of Intramolecular Pd-Catalyzed N-Arylation of Amides in the Synthesis of Nonaromatic Heterocycles
8.3.1 Applications in the Synthesis of Five-Membered N-Heterocycles
8.3.2 Application in the Synthesis of Six-Membered N-Heterocycles
8.3.3 Application in the Synthesis of Seven-Membered N-Heterocycles
8.4 Intramolecular Pd-Catalyzed Arylation of Sulfonamides
8.5 Applications of the Intramolecular Buchwald-Hartwig Amination in the Synthesis of Natural Products
8.6 Conclusion
References
Chapter 9 Synthesis of Nonaromatic Nitrogen Heterocycles via Singlet Oxygen
9.1 Introduction
9.2 Singlet Oxygen on Organic Synthesis
9.2.1 Oxidation of Bipyrroles
9.2.2 Synthesis of (R)-Methylnaltrexone
9.2.3 Synthesis of Glochidine and Glochidicine
9.2.4 Synthesis of ?-Lactams via One-pot Synthesis
9.2.5 Synthesis of the Melohenine B
9.2.6 Synthesis of Pyrrolidine Derivatives by [2?+?3] Cycloaddition, via 1O2 Mediated 1,3-Dipole
9.2.7 Synthesis of Pandamarine
9.2.8 Preparation of Bicyclic Lactams
9.2.9 Synthesis of Alkaloids
9.2.10 Synthesis of Azaspiro Frameworks
9.2.11 Preparation of Tetrahydropyranopyrrolones
9.2.12 Synthesis of 2-Oxindoles
9.2.13 Synthesis of Several Natural Products from an Amino Furan Derivative
9.2.14 Synthesis of Peptide-Fluorescent Probes
9.2.15 Synthesis of Tetrahydroquinolines
9.3 Conclusion
References
Chapter 10 Cobalt-Catalyzed Carbonylation for the Synthesis of N-Heterocyclic Compounds
10.1 Introduction
10.2 Cobalt-catalyzed Carbonylation for the Synthesis of N-Heterocyclic Compounds Using CO Gas as CO Source
10.3 Cobalt-Catalyzed Carbonylation for the Synthesis of N-Heterocycles Using CO Surrogates
10.4 Conclusions
Acknowledgments
References
Chapter 11 Enantioselective Synthesis of Nitrogen Heterocycles Using Chiral Hypervalent Iodine Reagents
11.1 Introduction
11.2 The Historical Development of Chiral Hypervalent Iodine Reagents
11.3 Synthesis with Chiral Hypervalent Iodine Reagents
11.3.1 Difunctionalization of Alkenes
11.3.1.1 Diamination
11.3.1.2 Oxyamination
11.3.1.3 Dioxycyclization of Amides
11.3.1.4 Cycloamination in the Synthesis of Piperidines and Their Derivatives
11.3.1.5 Aminofluorination
11.3.1.6 Aziridination
11.3.1.7 Thioamination
11.3.1.8 Aminoarylation
11.3.2 Dearomatization Reactions
11.3.3 a-Functionalization of Carbonyl Compounds
11.3.3.1 Spirocyclization Through C(sp2) H/C(sp3) H Coupling
11.3.3.2 Synthesis of Spirofurooxindoles via Cascade Oxidative C O and C C Bond Formation
11.4 Conclusion
Acknowledgments
References
Part III SPECIAL TECHNIQUES
Chapter 12 Synthesis of Bioactive Heterocycles Exploiting Modern Continuous Flow Chemistry
12.1 Introduction to Modern Flow Chemistry
12.2 Value of Heterocyclic Chemistry for Modern Drug Discovery Programs
12.3 Flow Synthesis of Three-Membered Nonaromatic Heterocycles
12.4 Flow Synthesis of Four-Membered Nonaromatic Heterocycles
12.5 Flow Synthesis of Five-Membered Nonaromatic Heterocycles
12.6 Flow Synthesis of Six-Membered Nonaromatic Heterocycles
12.7 Flow Synthesis of Seven-Membered Nonaromatic Heterocycles
12.8 Flow Synthesis of Macrocyclic Nonaromatic Heterocycles
12.9 Assessment of the Merits of Continuous Flow Processing for Heterocycle Synthesis - Summary and Conclusions
References
Chapter 13 The Electrochemical Synthesis of Nonaromatic N-Heterocycles
13.1 Introduction
13.2 Laws of Organic Electrosynthesis
13.2.1 Types of Electrolyses
13.2.2 Diagnostic Analytical Methods: Voltammetry
13.3 Construction of Three- and Four-Membered Nonaromatic Heterocycles
13.3.1 Aziridines
13.3.2 Epoxides
13.3.3 Azetidines
13.4 Construction of Five Six and Seven Membered Nonaromatic Heterocycles
13.4.1 Pyrrolidines
13.4.2 Indolines and Dihydrobenzofurans
13.4.3 Pyrrolidinones, 5-Membered Cyclic Carbamates and Derivatives
13.4.4 Tetrahydrooxazole and Tetrahydrooxazine Derivatives
13.4.5 Six-Membered Cyclic Amides, Carbamates, and Derivatives
13.5 Construction of Nonaromatic Heterocycles with Fused-Polycyclic Systems
13.5.1 Non-aromatic Heterocycles from Phtalimides and Succinimides
13.5.2 Polycyclic Peptides
13.5.3 Polyclic Ureas
13.5.4 Ring-Fused Quinones
13.6 Conclusion
References
Chapter 14 Asymmetric Organocatalysis in Alternative Media
14.1 Introduction
14.2 Water as Reaction Medium
14.3 Ionic Liquids as Alternative Media
14.4 Miscellaneous Alternative Reaction Media
14.4.1 Supercritical Carbon Dioxide (scCO2)
14.4.2 Polyethylene Glycols (PEGs)
14.4.3 Deep Eutectic Solvents (DES)
14.5 Conclusions
Acknowledgment
References
Part IV SYNTHETIC METHODS FOR SPECIAL COMPOUND CLASSES
Chapter 15 Strained Aziridinium Ion
15.1 Introduction
15.2 Formation of Aziridinium Ions
15.3 Ring Opening of Aziridinium Ion
15.4 Synthetic Applications
15.5 Bicyclic Aziridinium Ion and its Application
Acknowledgments
References
Chapter 16 Recent Advances on the Synthesis of Azepane-Based Compounds
16.1 Introduction
16.2 Azepane Synthesis
16.2.1 Synthesis of Substituted Azepanes
16.2.2 Synthesis of Ring-Fused Azepanes
16.2.3 Synthesis of Azepane-Based Alkaloids
16.3 Conclusions
References
Chapter 17 1,4-Diazepane Ring-Based Systems
17.1 Introduction
17.2 Reductive Amination
17.3 Mitsunobu Amination
17.4 1,3-Dipolar Cycloaddition
17.5 Multicomponent Reactions
17.6 Other Methods
17.7 Conclusions
References
Chapter 18 Transition Metal Promoted Synthesis of Isoindoline Derivatives
18.1 Introduction
18.2 Synthesis of Isoindolines
18.2.1 [2?+?2?+?2] Cycloaddition Reactions
18.2.1.1 [2?+?2?+?2] Rhodium Catalysed Cycloaddition Reactions
18.2.1.2 [2?+?2?+?2] Cobalt and Iridium Catalyzed Cycloaddition Reactions
18.2.1.3 [2?+?2?+?2] Ruthenium Catalyzed Cycloaddition Reactions
18.2.1.4 [2?+?2?+?2] Nickel and Palladium Catalyzed Cycloaddition Reactions
18.2.1.5 Other [2?+?2?+?2] Cycloaddition Reactions
18.2.2 Transition Metal-Promoted Diels-Alder reactions
18.2.2.1 Intramolecular Diels-Alder of N-Furfuryl N-Propargyl Amine Derivatives
18.2.2.2 Diels-Alder of N-2,4-Dienyl (or N-2-en-4-ynyl) N-Propargyl Amine Derivatives
18.2.2.3 Hexadehydro Diels-Alder (HDDA) of Triynes
18.2.3 Transition Metal-Promoted Cyclization of ortho-Substituted Benzyl Amines (and Derivatives)
18.2.3.1 Cyclization of ortho-Methyl or Ethyl-Substituted Benzyl Amines (and Derivatives)
18.2.3.2 Cyclization of ortho-Hydroxymethyl or Carbonyl/imino-Substituted Benzyl Amines (and Derivatives)
18.2.3.3 Cyclization of ortho-Alkenyl-Substituted Benzyl Amines (and Derivatives)
18.2.3.4 Cyclization of ortho-Alkynyl-Substituted Benzyl Amines (and Derivatives)
18.2.4 Transition Metal-Promoted 5-exo-dig Cyclization by C C Bond Formation
18.2.5 Miscellaneous
18.3 Conclusions and Perspectives
References
Chapter 19 1,2-Benzisothiazole 1,1-Dioxide (Saccharinate)-Based Compounds Synthesis, Reactivity and Applications
19.1 Introduction
19.2 Synthesis of Saccharinate-Based Conjugates
19.3 Applications
19.3.1 Ionic Liquids
19.3.2 Coordination Chemistry
19.3.3 Biological Activity and Medical Uses
19.4 Concluding Remarks
Acknowledgments
References
Chapter 20 Recent Developments for the Facile Synthesis of Triazole-Fused Heterocyles
20.1 Introduction
20.2 Recent Developments for Facile Synthesis and Applications of 1,2,4-Triazole-Fused Heterocycles
20.2.1 1,2,4-Triazole-Fused Heterocycles as Energetic Materials
20.2.2 1,2,4-Triazole-Fused Heterocycles as Building Blocks
20.3 Recent Developments for the Facile Synthesis of 1,2,3-Triazole-Fused Heterocycles
20.3.1 1,2,3-Triazole-Fused Heterocycles as Bioactive Scaffolds
20.3.2 1,2,3-Triazole-Fused Heterocycles as Functional Materials
20.4 Conclusion
References
Chapter 21 Recent Advances in the Design and Synthesis of Cyclic Peptidomimetics
21.1 Introduction
21.2 Click-Mediated Approaches for Cyclic Peptidomimetics
21.3 Enzyme-Mediated Approaches for Cyclic Peptidomimetics
21.4 Solid-Phase Synthesis of Cyclic Peptidomimetics
21.5 Conclusion
References
Index
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