Details

Isocyanide Chemistry

Applications in Synthesis and Material Science
1. Aufl.

von: V. Nenajdenko
174,99 €
Verlag:	Wiley-VCH (D)
Format:	PDF
Veröffentl.:	30.05.2012
ISBN/EAN:	9783527652563
Sprache:	englisch
Anzahl Seiten:	624

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Beschreibungen

Titelbeschreibung

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.

Inhaltsverzeichnis

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

Autorenportrait

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.