Advances in heterocyclic chemistry. Volume 125 /

Advances in Heterocyclic Chemistry, Volume 125 is the definitive series in the field - one of great importance to organic chemists, polymer chemists, and many biological scientists. Because biology and organic chemistry increasingly intersect, the associated nomenclature is being used more frequentl...

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Bibliographic Details
Corporate Author:	ScienceDirect (Online service)
Other Authors:	Scriven, Eric F. V. (Editor), Ramsden, Christopher A., 1946- (Editor)
Format:	eBook
Language:	English
Published:	Cambridge, MA : Academic Press is an imprint of Elsevier, 2018.
Series:	Advances in Heterocyclic Chemistry ; v. 125.
Subjects:	Heterocyclic chemistry. Chimie des composés hétérocycliques. Heterocyclic chemistry Electronic books.
Online Access:	Connect to the full text of this electronic book

Table of Contents:

Front Cover
Advances in Heterocyclic Chemistry
Copyright
Contents
Contributors
Preface
Chapter One: Diketene a Privileged Synthon in the Synthesis of Heterocycles. Part 2: Six-Membered Ring Heterocycles
1. Introduction
2. Synthesis of Six-Membered Heterocycles
2.1. Containing One Heteroatom
2.1.1. Oxygen
2.1.2. Nitrogen
2.1.3. Sulfur
2.2. Containing Two Heteroatoms
2.2.1. Nitrogen and Oxygen
2.2.2. Nitrogen and Sulfur
2.2.3. Oxygen and Sulfur
2.3. Containing Three Heteroatoms
3. Synthesis of Fused Polycyclic Heterocycles
4. Conclusion
Acknowledgments
References
Chapter Two: Recent Advances in the Synthesis of Piperidines: Functionalization of Preexisting Ring Systems
1. Introduction
2. Hydrogenations of Pyridine
2.1. Organocatalyzed Hydrogenations
2.1.1. Organocatalytic Asymmetric Hydrogenations
2.1.2. Organocatalytic Hydrogenations With Frustrated Lewis Pairs
2.2. Transition Metal-Catalyzed Hydrogenations
2.2.1. Heterogeneous Catalysis
2.2.1.1. Racemic Hydrogenations
2.2.1.2. Diastereoselective Hydrogenations
2.2.2. Homogeneous Catalysis
2.2.2.1. Achiral Hydrogenations
2.2.2.2. Enantioselective Hydrogenations
2.2.2.2.1. Rh-Catalyzed Asymmetric Hydrogenation
2.2.2.2.2. Ir-Catalyzed Asymmetric Hydrogenation
3. Functionalization of C
H Bond in Piperidines
3.1. Reactions of Electrophile With Alpha Aminocarbanion Species
3.2. Reactions of Nucleophiles With Iminium Ions
3.2.1. Transition Metal-Catalyzed Oxidation
3.2.1.1. With Chemical Oxidant
3.2.1.2. Without Chemical Oxidant
3.2.2. Chemical Oxidation
3.2.3. Redox-Neutral Oxidation
3.2.4. Electrochemical Oxidation
3.2.5. Visible Light-Induced Photocatalytic Oxidation
3.3. Reactions of Alpha Amino Radicals
3.4. Transition Metal-Catalyzed C
H Bond Activation.
3.4.1. Inner Sphere Mechanism
3.4.1.1. Oxidative Addition Into a C
H Bond
3.4.2. Outer Sphere Mechanism
3.4.2.1. Carbenoid and Nitrenoid Insertion Into a C
H Bond
4. Cross-Coupling of Halogenated Piperidines
4.1. Traditional Cross-Coupling
4.1.1. Suzuki Coupling
4.1.2. Negishi Coupling
4.1.3. Heck Coupling
4.1.4. Hiyama Coupling
4.1.5. Sonogashira Coupling
4.1.6. Kumada Coupling
4.2. Reductive Cross-Coupling
5. Preparation of Piperidines by Ring Expansion of 2-Substituted Pyrrolidines
5.1. Synthesis of 3-Hydroxypiperidines
5.2. Synthesis of 3-Aminoxypiperidines
5.3. Synthesis of 3-Halopiperidines
5.4. Synthesis of 3-Cyanopiperidines
6. Summary and Outlook
References
Further Reading
Chapter Three: Indazoles: Synthesis and Bond-Forming Heterocyclization
1. Introduction
1.1. Structure and Biological Activities of Indazoles
2. Synthetic Section
2.1. Formation of One Bond: Between Carbon and Nitrogen
2.1.1. Diazonium Salts
2.1.2. Nitrosamines
2.1.3. Oxone
2.1.4. Palladium-Catalyzed Reactions
2.1.5. Intramolecular Amination
2.1.6. Chromium Complexes
2.2. Between Two Nitrogens to Give a New N
N Bond
2.2.1. Nitro Compounds
2.2.2. Amino Compounds
3. Formation of Two Bonds
3.1. Reaction of Hydrazine Derivatives With1,3-Diketonic Compounds
3.1.1. 1,3-Diketones
3.1.2. Ketoesters, Ketoacetals, and Ketothioesters
3.1.3. Alkenones
3.1.4. Trifluoroacyl Ketones
3.1.5. Baylis-Hillman Adducts
3.1.6. Halo Aldehydes, Ketones, Acids, and Nitriles
4. Synthesis of Benzopyrano[4,3,2-cd]indazoles
5. Reaction of ortho-Substituted Compounds With Hydrazine
6. Miscellaneous Cyclizations
6.1. Palladium-Catalyzed Cyclization
6.2. Cyclization With 1,4-Benzo-, Naphtho-, and Quinones
6.3. 2+3 Cyclization
6.4. 4+1 Component Cyclization.
7. From Other Heterocycles
8. Synthesis of Thiazolo[3,4-b]indazoles
9. Reactions
9.1. Ring Reactions
9.1.1. At N-1
9.1.2. At N-2
9.1.3. At C-3
9.1.4. At C-5
9.1.5. At C-7
9.2. Substituent Reactions
9.2.1. At N-2 Substituent
9.2.2. At C-3 Substituent
9.2.2.1. Synthesis of Azatryptophanes and Amino Acid Derivatives
9.2.3. At C-5 Substituent
9.2.4. At C-7 Substituent
9.3. Anellations
9.3.1. 1,2-Anellation
9.3.2. 2,3-Anellation
9.3.3. 3,4-Anellation
9.3.4. 4,5-Anellation
9.3.5. 5,6-Anellation
9.3.6. 6,7-Anellation
10. Dehydrogenation
11. Cleavage
References
Further Reading
Chapter Four: The Chemistry of Sulfur-Containing [5,5]-Fused Ring Systems With a Bridgehead Nitrogen
1. Introduction
2. Pyrrolo[2,1-b]thiazoles
2.1. Synthesis
2.1.1. From Thiazole Precursors and Î±-Bromoketones
2.1.2. From Thiazoles
2.1.3. From Pyrrole Derivatives
2.1.4. From Other Derivatives
2.2. Functionalization
3. Pyrazolo[5,1-b]thiazoles
3.1. Synthesis and Functionalization
4. Imidazo[5,1-b]thiazoles
4.1. Synthesis and Functionalization
5. Imidazo[2,1-b]thiazoles
5.1. Synthesis
5.1.1. From 2-Aminothiazoles
5.1.2. From 2-Thioimidazoles
5.1.3. Multicomponent Reactions
5.1.4. From Ring-Closing and Ring-Opening Reactions
5.2. C-5 Functionalization
5.2.1. Carbonylation
5.2.2. C
H Arylation
5.2.3. Formylation
5.2.4. Nitrosation
5.2.5. Chlorination and Bromination
5.2.6. Trifluoromethylation
5.2.7. Sulfenylation/Thiocyanation/Selenylation
5.2.8. Phosphonation
5.2.9. Other C-5 Functionalization
5.3. C-2 Functionalization
5.3.1. C
H Arylation
5.3.2. C
H Alkenylation
5.3.3. Mannich Reaction
6. Thiazolo[3,2-b][1,2,4]triazoles
6.1. Synthesis
6.1.1. From Triazoles
6.1.2. Miscellaneous Methods.
6.2. Functionalization
7. Thiazolo[2,3-c][1,2,4]triazoles
7.1. Synthesis
7.1.1. From Triazoles
7.1.2. From Thiazoles
7.2. Functionalization
8. Imidazo[2,1-b]thiadiazoles
8.1. Synthesis
8.1.1. From Thiadiazoles
8.1.2. Multicomponent Reactions
8.2. C-5 Functionalization
8.2.1. Electrophilic Aromatic Substitution
8.2.2. CH Activation
8.3. C-2 Functionalization
9. Imidazo[1,2-d][1,2,4]thiadiazoles
9.1. Synthesis and Functionalization
10. Other [5,5]-Fused Ring Systems Contained Sulfur and Nitrogen
10.1. Thiazolo[3,2-d]tetrazoles
11. Concluding Remarks
References
Index
Back Cover.