Isocyanide Chemistry
Applications in Synthesis and Material Science
1. Edition July 2012
XVIII, 606 Pages, Hardcover
712 Pictures
30 tables
Handbook/Reference Book
ISBN:
978-3-527-33043-0
Wiley-VCH, Weinheim
Short Description
Filling a gap in the literature, the highly experienced and internationally renowned editor has brought together an equally distinguished author team to cover the topic in unrivaled depth, presenting all aspects of synthetic isocyanide chemistry.
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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.
PREFACE
CHIRAL NONRACEMIC ISOCYANIDES
Introduction
Simple Unfunctionalized Isocyanides
Isocyanides Containing Carboxylic, Sulfonyl, or Phosphonyl Groups
Isocyanides Containing Amino or Alcoholic Functionalities
Natural Isocyanides
Isocyanides Used in the Synthesis of Chiral Polyisocyanides
GENERAL ASPECTS OF ISOCYANIDE REACTIVITY
Introduction
Isocyanide?Cyanide Rearrangement
Oxidation/Reduction of the Isocyano Group
Reactions of Isocyanides with Electrophiles
Reactions of Isocyanides with Nucleophiles
Conclusions
Alpha-ACIDIC ISOCYANIDES IN MULTICOMPONENT CHEMISTRY
Introduction
Synthesis of a-Acidic Isocyanides
Reactivity of a-Acidic Isocyanides
MCRs Involving a-Acidic Isocyanides
Conclusions
SYNTHETIC APPLICATION OF ISOCYANOACETIC ACID DERIVATIVES
Introduction
Synthesis of a-Isocyanoacetate Derivatives
Alkylation of Isocyanoacetic Acid Derivatives
a-Isocyanoacetates as Michael Donors
Reaction of Isocyanoacetic Acids with Alkynes: Synthesis of Pyrroles
Reaction of Isocyanoacetic Acid Derivatives with Carbonyl Compounds and Imines
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
UGI AND PASSERINI REACTIONS WITH CARBOXYLIC ACID SURROGATES
Introduction
Carboxylic Acid Surrogates
Use of Mineral and Lewis Acids
Conclusions
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
MULTIPLE MULTICOMPONENT REACTIONS WITH ISOCYANIDES
Introduction
One-Pot Multiple IMCRs
Isocyanide-Based Multiple Multicomponent Macrocyclizations
Sequential Isocyanide-Based MCRs
Conclusions
ZWITTERIONS AND ZWITTERION-TRAPPING AGENTS IN ISOCYANIDE CHEMISTRY
Introduction
Generation of Zwitterionic Species by the Addition of Isocyanides to Alkynes
Generation of Zwitterionic Species by the Addition of Isocyanides to Arynes
Generation of Zwitterionic Species by the Addition of Isocyanides to Electron-Deficient Olefins
Miscellaneous Reports for the Generation of Zwitterionic Species
Isocyanides as Zwitterion-Trapping Agents
Conclusions
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
APPLICATIONS OF ISOCYANIDES IN IMCRS FOR THE RAPID GENERATION OF MOLECULAR DIVERSITY
Introduction
Ugi/Deprotect/Cyclize (UDC) Methodology
Secondary Reactions of Ugi Products
The Bifunctional Approach (BIFA)
SYNTHESIS OF PYRROLES AND THEIR DERIVATIVES FROM ISOCYANIDES
Introduction
Synthesis of Pyrroles Using TosMIC
Synthesis of Pyrroles Using Isocyanoacetates
Synthesis of Porphyrins and Related Compounds
Conclusion
ISOCYANIDE-BASED MULTICOMPONENT REACTIONS TOWARDS BENZODIAZEPINES
Introduction
1,4-Benzodiazepine Scaffolds Assembled via IMCR Chemistry
1,5-Benzodiazepine Scaffolds Assembled via IMCR Chemistry
Outlook
APPLICATIONS OF ISOCYANIDES IN THE SYNTHESIS OF HETEROCYCLES
Introduction
Furans
Pyrroles
Oxazoles
Isoxazoles
Thiazoles 4
Imidazoles
Pyrazoles
Oxadiazoles and Triazoles
Tetrazoles
Benzofurans and Benzimidazoles
Indoles
Quinolines
Quinoxaline
RENAISSANCE OF ISOCYANOARENES AS LIGANDS IN LOW-VALENT ORGANOMETALLICS
Historical Perspective
Isocyanidemetalates and Related Low-Valent Complexes
Coordination and Surface Chemistry of Nonbenzenoid Isocyanoarenes
Conclusions and Outlook
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
POLYISOCYANIDES
Introduction
The Polymerization Mechanism
Conformation of the Polymeric Backbone
Polyisocyanopeptides
Polyisocyanides as Scaffolds for the Anchoring of Chromophoric Molecules
Functional Polyisocyanides
Conclusions and Outlook
CHIRAL NONRACEMIC ISOCYANIDES
Introduction
Simple Unfunctionalized Isocyanides
Isocyanides Containing Carboxylic, Sulfonyl, or Phosphonyl Groups
Isocyanides Containing Amino or Alcoholic Functionalities
Natural Isocyanides
Isocyanides Used in the Synthesis of Chiral Polyisocyanides
GENERAL ASPECTS OF ISOCYANIDE REACTIVITY
Introduction
Isocyanide?Cyanide Rearrangement
Oxidation/Reduction of the Isocyano Group
Reactions of Isocyanides with Electrophiles
Reactions of Isocyanides with Nucleophiles
Conclusions
Alpha-ACIDIC ISOCYANIDES IN MULTICOMPONENT CHEMISTRY
Introduction
Synthesis of a-Acidic Isocyanides
Reactivity of a-Acidic Isocyanides
MCRs Involving a-Acidic Isocyanides
Conclusions
SYNTHETIC APPLICATION OF ISOCYANOACETIC ACID DERIVATIVES
Introduction
Synthesis of a-Isocyanoacetate Derivatives
Alkylation of Isocyanoacetic Acid Derivatives
a-Isocyanoacetates as Michael Donors
Reaction of Isocyanoacetic Acids with Alkynes: Synthesis of Pyrroles
Reaction of Isocyanoacetic Acid Derivatives with Carbonyl Compounds and Imines
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
UGI AND PASSERINI REACTIONS WITH CARBOXYLIC ACID SURROGATES
Introduction
Carboxylic Acid Surrogates
Use of Mineral and Lewis Acids
Conclusions
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
MULTIPLE MULTICOMPONENT REACTIONS WITH ISOCYANIDES
Introduction
One-Pot Multiple IMCRs
Isocyanide-Based Multiple Multicomponent Macrocyclizations
Sequential Isocyanide-Based MCRs
Conclusions
ZWITTERIONS AND ZWITTERION-TRAPPING AGENTS IN ISOCYANIDE CHEMISTRY
Introduction
Generation of Zwitterionic Species by the Addition of Isocyanides to Alkynes
Generation of Zwitterionic Species by the Addition of Isocyanides to Arynes
Generation of Zwitterionic Species by the Addition of Isocyanides to Electron-Deficient Olefins
Miscellaneous Reports for the Generation of Zwitterionic Species
Isocyanides as Zwitterion-Trapping Agents
Conclusions
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
APPLICATIONS OF ISOCYANIDES IN IMCRS FOR THE RAPID GENERATION OF MOLECULAR DIVERSITY
Introduction
Ugi/Deprotect/Cyclize (UDC) Methodology
Secondary Reactions of Ugi Products
The Bifunctional Approach (BIFA)
SYNTHESIS OF PYRROLES AND THEIR DERIVATIVES FROM ISOCYANIDES
Introduction
Synthesis of Pyrroles Using TosMIC
Synthesis of Pyrroles Using Isocyanoacetates
Synthesis of Porphyrins and Related Compounds
Conclusion
ISOCYANIDE-BASED MULTICOMPONENT REACTIONS TOWARDS BENZODIAZEPINES
Introduction
1,4-Benzodiazepine Scaffolds Assembled via IMCR Chemistry
1,5-Benzodiazepine Scaffolds Assembled via IMCR Chemistry
Outlook
APPLICATIONS OF ISOCYANIDES IN THE SYNTHESIS OF HETEROCYCLES
Introduction
Furans
Pyrroles
Oxazoles
Isoxazoles
Thiazoles 4
Imidazoles
Pyrazoles
Oxadiazoles and Triazoles
Tetrazoles
Benzofurans and Benzimidazoles
Indoles
Quinolines
Quinoxaline
RENAISSANCE OF ISOCYANOARENES AS LIGANDS IN LOW-VALENT ORGANOMETALLICS
Historical Perspective
Isocyanidemetalates and Related Low-Valent Complexes
Coordination and Surface Chemistry of Nonbenzenoid Isocyanoarenes
Conclusions and Outlook
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
POLYISOCYANIDES
Introduction
The Polymerization Mechanism
Conformation of the Polymeric Backbone
Polyisocyanopeptides
Polyisocyanides as Scaffolds for the Anchoring of Chromophoric Molecules
Functional Polyisocyanides
Conclusions and Outlook
Valentine G. Nenajdenko became full Professor of Organic Chemistry at the Department of Chemistry of Moscow State University. His scientific interests include organic synthesis, asymmetric catalysis, the chemistry of sulfur and fluorine containing compounds, heterocyclic chemistry, multicomponent reactions. He was the winner of the Academiae Europeae Award in 1997, the Russian President Award in 1996, the Prize for the best scientific work at the Department of Chemistry of Moscow State University in 2001 and 2007, the Shuvalov Award in 2001, the Russian President Award in 2004, Russian Science Support Foundation in 2005, Moscow State University Awards in 2006, 2007 and 2008.
