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E-grāmata: Heterocycles: Synthesis, Catalysis, Sustainability, and Characterization [Wiley Online]

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  • Formāts: 560 pages
  • Izdošanas datums: 20-Jul-2022
  • Izdevniecība: Blackwell Verlag GmbH
  • ISBN-10: 3527832009
  • ISBN-13: 9783527832002
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Heterocycles: Synthesis, Catalysis, Sustainability, and CharacterizationPalielināt
  • Formāts: 560 pages
  • Izdošanas datums: 20-Jul-2022
  • Izdevniecība: Blackwell Verlag GmbH
  • ISBN-10: 3527832009
  • ISBN-13: 9783527832002
Citas grāmatas par šo tēmu:
Wiley Online E-booksMore info about Wiley Online
Rokasgrāmatas mājas lapa: https://onlinelibrary.wiley.com/doi/book/10.1002/9783527832002
Heterocycles

A must-read handbook on heterocycle chemistry with a focus on sustainability

Heterocycles feature prominently in our daily life—they are essential for pharmaceuticals, agrochemicals, and fine chemicals. More, numerous natural, bioactive products contain heterocyclic compounds. As a result, heterocyclic chemistry continues to be one of the most important areas of study in organic chemistry.

Heterocycles provides an important reference on a wide range of topics relating to heterocyclic chemistry, with a heavy emphasis on sustainable methods and greener syntheses. The book describes state-of-the-art synthetic methods, such as photochemical reactions, dearomatization reactions, organocatalysis, transition metal catalysis, and biocatalysis. It also covers:

  • Sustainable methods, like flow chemistry, mechanochemistry, and multicomponent synthesis
  • Strategies for the synthesis of heterocyclic macrocycles and medium-sized rings
  • Characterization of heterocyclic compounds

Heterocycles is a useful reference for organic chemists, natural products chemists, catalytic chemists, and medicinal chemists in academia and industry.

Preface xi
1 Heterocyclic Compounds in Enantioselective Photochemical Reactions
1(26)
Norbert Hoffmann
1.1 Introduction
1(1)
1.2 Asymmetric Catalysis with Chiral Templates
2(5)
1.3 Asymmetric Photo-Enzyme Catalysis
7(2)
1.4 Asymmetric Photochemical Reactions in Crystals
9(3)
1.5 Crystalline Inclusion Complexes
12(1)
1.6 Inclusion in Zeolites
13(1)
1.7 Memory of Chirality
14(1)
1.8 Conclusion and Perspectives
15(12)
References
16(11)
2 Heterocycles via Dearomatization Reactions
27(32)
Alexey M. Starosotnikov
Maxim A. Bastrakov
2.1 Introduction
27(1)
2.2 Annulation of Heterocycles via Dearomative Cycloaddition to Arenes and Hetarenes
28(14)
2.2.1 [ 3+2] Cycloaddition
28(8)
2.2.2 [ 4+2] Cycloaddition
36(5)
2.2.3 Other Cycloadditions
41(1)
2.3 Intramolecular Addition to Aromatic Double Bonds Leading to Heterocycles
42(3)
2.4 Dearomative Spirocyclizations
45(6)
2.5 Conclusion and Perspectives
51(8)
Acknowledgments
51(1)
References
51(8)
3 Strategies for the Synthesis of Heterocyclic Macrocycles and Medium-Sized Rings
59(26)
William P. Unsworth
Thomas C. Stephens
3.1 Introduction
59(2)
3.2 High Dilution and Pseudo-High Dilution Methods
61(6)
3.2.1 Traditional High Dilution/Slow Addition Methods
61(4)
3.2.2 Solid-Supported Methods
65(1)
3.2.3 Phase Separation
65(2)
3.3 Methods Designed to Impart More Favorable Cyclization Conformations
67(4)
3.3.1 The Importance of Conformation on Macrocyclization
67(2)
3.3.2 Structural Features to Bias Cyclization Conformation
69(2)
3.3.3 Templated Macrocyclization
71(1)
3.4 Ring-Expansion Methods
71(4)
3.5 Medium-Sized Rings: Special Cases
75(2)
3.6 Conclusions and Perspectives
77(8)
References
78(7)
4 Organocatalysis in Synthetic Heterocyclic Chemistry
85(32)
Angel Cores
Mercedes Villacampa
J. Carlos Menendez
4.1 Introduction
85(2)
4.2 Organocatalytic Synthesis of Five-Membered Heterocycles
87(3)
4.2.1 Pyrroles and Pyrrolidines
87(2)
4.2.2 Furan and Benzofuran Derivatives
89(1)
4.3 Organocatalytic Synthesis of Six-Membered Heterocycles
90(14)
4.3.1 Pyridines, Dihydropyridines, and Piperidines
90(8)
4.3.2 Fused Pyridine Derivatives
98(3)
4.3.3 Pyrimidines
101(1)
4.3.4 Pyran and Fused Pyrans
101(3)
4.4 Organocatalytic Synthesis of Seven-Membered Heterocycles
104(3)
4.4.1 Diazepines and Fused Diazepines
104(2)
4.4.2 Thiazepines and Fused Thiazepines
106(1)
4.5 Organocatalytic Synthesis of Polyheterocyclic, Bridged, and Spiro Compounds
107(4)
4.6 Conclusion and Perspectives
111(6)
Acknowledgments
111(1)
References
111(6)
5 Transition Metal Catalysis in Synthetic Heterocyclic Chemistry
117(42)
Dina Murtinho
M. Elisa da Silva Serra
5.1 Introduction
117(1)
5.2 Copper-Catalyzed Synthesis of Heterocycles
118(9)
5.2.1 Fused Heterocycles
118(2)
5.2.2 Five- and Six-Membered N- and N,N-Heterocycles
120(6)
5.2.3 Five- and Six-Membered N,0-Heterocycles
126(1)
5.3 Pd-Catalyzed Heterocycle Synthesis
127(15)
5.3.1 Nitrogen Heterocycles
128(7)
5.3.2 Oxygen Heterocycles
135(5)
5.3.3 N,0-Heterocycles
140(2)
5.4 Conclusion and Perspectives
142(17)
Acknowledgments
142(1)
References
142(17)
6 Biocatalytic Synthesis of Heterocycles
159(56)
Alina Nastke
Harald Groger
6.1 Introduction
159(1)
6.2 Three-Membered Ring Heterocycles
160(9)
6.2.1 N-Heterocycles
160(1)
6.2.2 O-Heterocycles
160(1)
6.2.2.1 Halohydrin Dehalogenases
161(1)
6.2.2.2 FAD-Dependent Monooxygenases
162(2)
6.2.2.3 Heme-Dependent Monooxygenases
164(2)
6.2.2.4 Peroxygenases
166(3)
6.3 Four-Membered Ring Heterocycles
169(2)
6.4 Five-Membered Ring Heterocycles
171(24)
6.4.1 N-Heterocycles
171(1)
6.4.1.1 Aliphatic Heterocycles
171(3)
6.4.1.2 Lactams
174(4)
6.4.1.3 Aromatic Heterocycles
178(3)
6.4.2 O-Heterocycles
181(1)
6.4.2.1 Aliphatic Heterocycles
181(3)
6.4.2.2 Lactones
184(6)
6.4.2.3 Aromatic Heterocycles
190(4)
6.4.3 S-Heterocycles
194(1)
6.5 Six-Membered Ring Heterocycles
195(8)
6.5.1 N-Heterocycles
195(8)
6.5.2 O-Heterocycles
203(1)
6.6 Conclusion and Perspectives
203(12)
References
203(12)
7 Multicomponent Synthesis of Heterocycles
215(62)
Carolina S. Marques
Elisabete P. Carreiro
Antonio P. S. Teixeira
7.1 Introduction
215(1)
7.2 Three-Membered Ring Heterocycles
216(3)
7.3 Four-Membered Ring Heterocycles
219(3)
7.4 Five-Membered Ring Heterocycles
222(15)
7.4.1 Five-Membered Ring Heterocycles with One Heteroatom
223(9)
7.4.2 Five-Membered Ring Heterocycles with Two Heteroatoms
232(4)
7.4.3 Five-Membered Ring Heterocycles with Three and Four Heteroatoms
236(1)
7.5 Six-Membered Ring Heterocycles
237(12)
7.5.1 Six-Membered Ring Heterocycles with One Heteroatom
237(6)
7.5.2 Six-Membered Ring Heterocycles with Two Heteroatoms
243(4)
7.5.3 Six-Membered Ring Heterocycles with Three Heteroatoms
247(2)
7.6 Seven-Membered Ring Heterocycles
249(4)
7.7 Conclusions and Perspectives
253(24)
Acknowledgments
253(1)
References
254(23)
8 Heterocyclic Compounds from Renewable Resources
277(24)
Giuseppe Mele
Selma E. Mazzetto
Diego Lomonaco
8.1 Introduction
277(1)
8.2 Three-, Five-, Six-, and Seven-Membered Ring Heterocycles Based on CNSL
278(8)
8.2.1 Oxiranes (Epoxides)
278(3)
8.2.2 Benzoxazines
281(3)
8.2.3 Cardanol-Based Lactones
284(1)
8.2.4 Cardanol-Based Amphiphilic Heterocycles
284(1)
8.2.5 Fulleropyrolidines
285(1)
8.2.6 Triazoles and Pyrimidine Hybrids
286(1)
8.3 Porphyrins and Phthalocyanines Derived from Cardanol-Based Precursors
286(7)
8.3.1 Syntheses of Porphyrins (Pps) and Phthalocyanines (Pes) from Cardanol-Based Precursors
286(2)
8.3.2 Applications of Cardanol-Derived Porphyrins (Pps) and Phthalocyanines (Pes)
288(1)
8.3.2.1 Langmuir-Blodgett Films
288(1)
8.3.2.2 Superparamagnetic Fluorescent Nanosystems
289(1)
8.3.2.3 Corrosion Protection
289(1)
8.3.2.4 Organic Light-Emitting Diodes (OLEDs)
289(1)
8.3.2.5 Photodynamic Therapy
290(1)
8.3.2.6 Composites Semiconductor@Sensitizer for Enhancing Photocatalytic Processes
290(1)
8.3.2.7 Photo-ignition of Carbon Nanotubes/Ferrocene/Porphyrin Under LED Irradiation
291(1)
8.3.2.8 Intercalation of Pps into Vesicular Nanosystems
292(1)
8.3.2.9 Nanomaterials Based on Fe3O4 and Phthalocyanines Derived from CNSL
292(1)
8.4 Conclusions and Perspectives
293(8)
Acknowledgments
293(1)
References
293(8)
9 Synthesis of Heterocycles in Nonconventional Bio-based Reaction Media
301(38)
Anton V. Dolzhenko
9.1 Introduction
301(1)
9.2 Heterocyclizations in Glycerol
302(11)
9.2.1 Synthesis of Five-Membered Heterocycles in Glycerol
303(5)
9.2.2 Synthesis of Six-Membered Heterocycles in Glycerol
308(4)
9.2.3 Synthesis of Seven-Membered Heterocycles in Glycerol
312(1)
9.3 Heterocyclizations in Lactic Acid
313(4)
9.3.1 Synthesis of Five-Membered Heterocycles in Lactic Acid
313(2)
9.3.2 Synthesis of Six-Membered Heterocycles in Lactic Acid
315(2)
9.4 Heterocyclizations in γ-Valerolactone
317(5)
9.4.1 Synthesis of Five-Membered Heterocycles in γ-Valerolactone
318(2)
9.4.2 Synthesis of Six-Membered Heterocycles in γ-Valerolactone
320(2)
9.5 Heterocyclizations in 2-Methyltetrahydrofuran
322(5)
9.5.1 Synthesis of Five-Membered Heterocycles in 2-Methyltetrahydrofuran
323(2)
9.5.2 Synthesis of Six-Membered Heterocycles in 2-Methyltetrahydrofuran
325(2)
9.6 Heterocyclizations in Miscellaneous Unconventional Bio-based Media
327(3)
9.7 Conclusion and Perspectives
330(9)
Acknowledgments
330(1)
References
330(9)
10 Mechanochemistry in Heterocyclic Synthesis
339(32)
Vjekoslav Strukil
Davor Margetic
10.1 Introduction
339(2)
10.2 Mechanosynthesis of N-Heterocycles
341(14)
10.2.1 Five-Membered Ring Heterocycles
341(10)
10.2.2 Six-Membered Ring Heterocycles
351(3)
10.2.3 Porphyrins
354(1)
10.3 Mechanosynthesis of O-, S-, and Other Heterocycles
355(8)
10.3.1 Three-Membered Ring Heterocycles
355(1)
10.3.2 Five-Membered Ring Heterocycles
356(3)
10.3.3 Six-Membered Ring Heterocycles
359(4)
10.3.4 Eight-Membered Ring Heterocycles
363(1)
10.4 Conclusions and Perspectives
363(8)
References
364(7)
11 Flow Chemistry: Sequential Flow Processes for the Synthesis of Heterocycles
371(30)
Pedro Brandao
Marta Pineiro
Teresa M.V.D. Pinho e Melo
11.1 Introduction
371(1)
11.2 Flow Synthesis of Heterocycles
372(19)
11.2.1 Three-Membered Ring Heterocycles
372(2)
11.2.2 Four-Membered Ring Heterocycles
374(1)
11.2.3 Five-Membered Ring Heterocycles
374(10)
11.2.4 Six-Membered Ring Heterocycles
384(6)
11.2.5 Seven-Membered Ring Heterocycles
390(1)
11.3 Conclusions and Perspectives
391(10)
Acknowledgments
391(1)
References
391(10)
12 Matrix Isolation in Heterocyclic Chemistry
401(52)
Jose P. L. Roque
Claudio M. Nunes
Rui Fausto
12.1 Introduction
401(2)
12.2 Structural Characterization
403(9)
12.3 UV-Induced Photochemical Reactivity
412(12)
12.4 Thermal Reactivity
424(5)
12.5 IR-Induced Processes
429(6)
12.6 Tunneling in Heterocyclic Chemistry
435(9)
12.7 Conclusion and Perspectives
444(9)
Acknowledgments
445(1)
References
445(8)
13 NMR Structural Characterization of Oxygen Heterocyclic Compounds
453(72)
Ricardo A.L.S. Santos
Diana C.G.A. Pinto
Artur M.S. Silva
13.1 Introduction
453(1)
13.2 Three-Membered Heterocyclic Compounds
454(5)
13.3 Four-Membered Heterocyclic Compounds
459(7)
13.4 Five-Membered Heterocyclic Compounds
466(11)
13.5 Six-Membered Heterocyclic Compounds
477(17)
13.6 Chromene and Xanthene-Related Compounds
494(11)
13.7 Conclusions and Perspectives
505(20)
Acknowledgments
506(1)
References
506(19)
Index 525
Teresa M.V.D. Pinho e Melo is an Associate Professor at the University of Coimbra, Portugal. She is Head of the Organic Chemistry Research Group of the Coimbra Chemistry Centre and her research interests are in the area of synthetic and mechanistic heterocyclic chemistry as well as medicinal chemistry.

Marta Pineiro is an Assistant Professor at the University of Coimbra, Portugal. Her research interests are in the area of sustainable organic synthesis, microwave-assisted organic synthesis, mechanochemistry, and synthesis and applications of heterocycles with unique photophysical properties.
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