Isocyanide Chemistry: Applications in Synthesis and Material Science

دسته بندی: شیمی ارگانیک
ویرایش:  
نویسندگان: Nenajdenko V.  
سری:  
 
ناشر:  
سال نشر:  
تعداد صفحات: 599 
زبان: English 
فرمت فایل : PDF (درصورت درخواست کاربر به PDF، EPUB یا AZW3 تبدیل می شود) 
حجم فایل: 9 مگابایت 

قیمت کتاب (تومان) : 51,000

Wiley-VCH Verlag GmbH & Co. KGaA, 2012. — 587 p. The efficacy of isocyanide reactions in the synthesis of natural or naturallike products has resulted in a renaissance of isocyanide chemistry. Now isocyanides are widely used in different branches of organic, inorganic, coordination, combinatorial and medicinal chemistry
This invaluable reference is the only book to cover the topic in such depth, presenting all aspects of synthetic isonitrile chemistry. The highly
experienced and internationally renowned editor has brought together an equally distinguished team of authors who cover multicomponent
reactions, isonitriles in total synthesis, isonitriles in polymer chemistry and much more. Contents
Chiral Nonracemic Isocyanides
Introduction
Simple Unfunctionalized Isocyanides
Isocyanides Containing Carboxylic, Sulfonyl, or Phosphonyl Groups
α-Isocyano Esters
α-Isocyano Amides
Other Isocyano Esters or Amides
Chiral Sulfonylmethyl or Phosphonylmethyl Isocyanides
Isocyanides Containing Amino or Alcoholic Functionalities
Chiral Amino or Azido Isocyanides
Chiral Hydroxy Isocyanides
Natural Isocyanides
Isolation and Natural Sources
Synthesis of Naturally Occurring Isocyanides
Isocyanides Used in the Synthesis of Chiral Polyisocyanides
Properties
Synthesis
Applications
References
General Aspects of Isocyanide Reactivity
Introduction
Isocyanide–Cyanide Rearrangement
Oxidation/Reduction of the Isocyano Group
Oxidation of the Isocyano Group
Reactions with Sulfur and Selenium
Reduction of the Isocyano Group
Reactions of Isocyanides with Electrophiles
Reaction with Acids
Reactions with Halogens and Acyl Halides
Reactions with Activated Alkenes and Alkynes
Reactions with Carbonyl Compounds and Imines
Reactions with Activated Heterocumulens
Reactions of Isocyanides with Nucleophiles
Reactions with Organometallic Compounds
Reactions with Hydroxide, Alcohols, and Amines
Conclusions
References
α-Acidic Isocyanides in Multicomponent Chemistry
Introduction
Synthesis of α-Acidic Isocyanides
Reactivity of α-Acidic Isocyanides
MCRs Involving α-Acidic Isocyanides
van Leusen Imidazole MCR
2,6,7-Trisubstituted Quinoxaline MCR
4,5-Disubstituted Oxazole MCR
Nitropyrrole MCR
2,4,5-Trisubstituted Oxazole MCR
2,4,5-Trisubstituted Oxazoles
Variations on the 2,4,5-Trisubstituted Oxazole MCR
Oxazole MCR and In-Situ Domino Processes
Imidazoline MCR
Imidazoline MCR in the Union of MCRs
Dihydropyridone MCR
Conclusions
References
Synthetic Application of Isocyanoacetic Acid Derivatives
Introduction
Synthesis of α-Isocyanoacetate Derivatives
Alkylation of Isocyanoacetic Acid Derivatives
α-Isocyanoacetates as Michael Donors
Reaction of Isocyanoacetic Acids with Alkynes: Synthesis of Pyrroles
Reaction of Isocyanoacetic Acid Derivatives with Carbonyl Compounds and Imines
Aldol-Type Reaction of Isocyanoacetic Acids with Aldehydes: Synthesis of Oxazolines
Contents VII
Transition Metal-Catalyzed Aldol-Type Reactions
Reaction of Isocyanoacetic Acids with Imines: Imidazoline Formation
Reaction with Acylating Agents
Multicomponent Reactions of Isocyanoacetic Acid Derivatives
Chemistry of Isocyanoacetates Bearing an Additional Functional Group
Reactions of Isocyanoacetic Acids with Sulfur Electrophiles
Miscellaneous Reactions
Concluding Remarks
Notes Added in Proof
References
Ugi and Passerini Reactions with Carboxylic Acid Surrogates
Introduction
Carboxylic Acid Surrogates
Thiocarboxylic Acids
Carbonic Acid and Derivatives
Selenide and Sulfi de
Silanol
Isocyanic Acid and Derivatives
Hydrazoic Acid
Phenols and Derivatives
Cyanamide
Use of Mineral and Lewis Acids
Ugi and Passerini Reactions Triggered by Mineral Acids
Ugi and Passerini Reactions Triggered by Lewis Acids
Conclusions
References
Amine (Imine) Component Surrogates in the Ugi Reaction and Related Isocyanide-Based Multicomponent Reactions
Introduction
Hydroxylamine Components in the Ugi Reaction
Hydrazine Components in the Ugi Reaction
Miscellaneous Amine Surrogates for the Ugi Reaction
Activated Azines in Reactions with Isocyanides
Enamines, Masked Imines, and Cyclic Imines in the Ugi Reaction
Concluding Remarks
Acknowledgments
References
VIII Contents
Multiple Multicomponent Reactions with Isocyanides
Ludger A. Wessjohann, Ricardo A.W. Neves Filho, and Daniel G. Rivera
Introduction
One-Pot Multiple IMCRs
Synthesis of Multivalent Glycoconjugates
Synthesis of Hybrid Peptide–Peptoid Podands
Covalent Modifi cation and Immobilization of Proteins
Assembly of Polysaccharide Networks as Synthetic Hydrogels
Synthesis of Macromolecules by Multicomponent Polymerization
Isocyanide-Based Multiple Multicomponent Macrocyclizations
Synthesis of Hybrid Macrocycles by Double Ugi-4CR-Based Macrocyclizations
Synthesis of Macrobicycles by Threefold Ugi-4CR-Based Macrocyclization
Sequential Isocyanide-Based MCRs
Sequential Approaches to Linear and Branched Scaffolds
Sequential Approaches to Macrocycles
Convergent Approach to Natural Product Mimics
Conclusions
References
Zwitterions and Zwitterion-Trapping Agents in Isocyanide Chemistry
Introduction
Generation of Zwitterionic Species by the Addition of Isocyanides to Alkynes
CH-Acids as Zwitterion-Trapping Agents
NH-Acids as Zwitterion-Trapping Agents
OH-Acids as Zwitterion-Trapping Agents
Carbonyl Compounds as Zwitterion-Trapping Agents
Imine Compounds as Zwitterion-Trapping Agents
Electron-Defi cient Olefi ns as Zwitterion-Trapping Agents
Miscellaneous Compounds as Zwitterion-Trapping Agents
Generation of Zwitterionic Species by the Addition of Isocyanides to Arynes
Generation of Zwitterionic Species by the Addition of Isocyanides to
Electron-Defi cient Olefi ns
Miscellaneous Reports for the Generation of Zwitterionic Species
Isocyanides as Zwitterion-Trapping Agents
Conclusions
Acknowledgments
References
Contents IX
Recent Progress in Nonclassical Isocyanide-Based MCRs
Introduction
Type I MCRs: Isocyanide Attack on Activated Species
Type II MCRs: Isocyanide Activation
Type III MCRs: Formal Isocyanide Insertion Processes
Conclusions
Acknowledgments
References
Applications of Isocyanides in IMCRs for the Rapid Generation of Molecular Diversity
Introduction
Ugi/Deprotect/Cyclize (UDC) Methodology
Ugi-4CC: One Internal Nucleophile
TMSN3-Modifi ed Ugi-4CC: One Internal Nucleophile
Ugi-4CC: Two Internal Nucleophiles
Ugi-4CC: Three Internal Nucleophiles
Ugi-5CC: One Internal Nucleophile
Secondary Reactions of Ugi Products
Nucleophilic Additions and Substitutions
Alkylations
Mitsunobu Reactions
Lactonization and Lactamization
Base- or Acid-Promoted Condensations
Nucleophilic Aromatic Substitutions
Palladium-Mediated Reactions
Ring-Closing Metatheses
Staudinger–aza-Wittig Reactions
Cycloadditions
The Bifunctional Approach (BIFA)
Applications of Amino Acids
Applications of Cyclic Imines
Applications of Tethered Aldehyde and Keto Acids
Heterocyclic Amidines as a Tethered Ugi Input
Combined Bifunctional and Post-Condensation Modifi cations
Acknowledgments
Abbreviations
References
X Contents
Synthesis of Pyrroles and Their Derivatives from Isocyanides
Introduction
Synthesis of Pyrroles Using TosMIC
Synthesis of Pyrroles Using Isocyanoacetates
Synthesis from Nitroalkenes
Synthesis from α,β-Unsaturated Sulfones
Synthesis from Alkynes
Synthesis from Aromatic Nitro Compounds: Isoindole Derivatives
Synthesis of Porphyrins and Related Compounds
Tetramerization
Meso-Tetraarylporphyrins via the Lindsey Procedure
[3+2] and [2+2] Methods
Expanded, Contracted, and Isomeric Porphyrins
Functional Dyes from Pyrroles
Conclusion
References
Isocyanide-Based Multicomponent Reactions towards
Benzodiazepines
Introduction
1,4-Benzodiazepine Scaffolds Assembled via IMCR Chemistry
Two-Ring Systems
Fused-Ring Systems
1,5-Benzodiazepine Scaffolds Assembled via IMCR Chemistry
Outlook
References
Applications of Isocyanides in the Synthesis of Heterocycles
Introduction
Furans
Pyrroles
Oxazoles
Isoxazoles
Thiazoles
Imidazoles
Pyrazoles
Oxadiazoles and Triazoles
Tetrazoles
Benzofurans and Benzimidazoles
Indoles
Quinolines
Quinoxaline
Abbreviations
References
Renaissance of Isocyanoarenes as Ligands in Low-Valent Organometallics
Historical Perspective
Isocyanidemetalates and Related Low-Valent Complexes
Introduction
Four-Coordinate Isocyanidemetalates and Redox-Related Complexes
Five-Coordinate Isocyanidemetalates
Six-Coordinate Isocyanidemetalates and Redox-Related Complexes
Coordination and Surface Chemistry of Nonbenzenoid Isocyanoarenes
Isocyanoazulenes
Organometallic η5 -Isocyanocyclopentadienides
Homoleptic Complexes of Nonbenzenoid Isocyanoarenes
Bridging Nonbenzenoid Isocyanoarenes
Self-Assembled Monolayer Films of Nonbenzenoid Isocyano- and Diisocyanoarenes on Gold Surfaces
Conclusions and Outlook
Acknowledgments
References
Carbene Complexes Derived from Metal-Bound Isocyanides: Recent Advances
Introduction
Coupling of the Isocyanide Ligand with Simple Amines or Alcohols
Coupling of the Isocyanide Ligand with Functionalized Amines or Alcohols
Coupling of the Isocyanide Ligand with a Hydrazine or Hydrazone
Coupling of the Isocyanide Ligand with an Imine or Amidine
Intramolecular Cyclizations of Functionalized Isocyanide Ligands
Coupling of Isocyanides with Dipoles
Other Reactions
Final Remarks
Acknowledgments
References
XII Contents
Polyisocyanides
Niels Akeroyd, Roeland J.M. Nolte, and Alan E. Rowan
Introduction
Chiral Polymers
Polyisocyanides and Their Monomers
The Polymerization Mechanism
Conformation of the Polymeric Backbone
Polyisocyanopeptides
Polyisocyanides as Scaffolds for the Anchoring of Chromophoric Molecules
Functional Polyisocyanides
Conclusions and Outlook
References