Isocyanide Chemistry - Applications in Synthesis and Material Science

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 highlyexperienced and internationally renowned editor has brought together an equally distinguished team of authors who cover multicomponentreactions, isonitriles in total synthesis, isonitriles in polymer chemistry and much more.

Sommario

PREFACE CHIRAL NONRACEMIC ISOCYANIDESIntroduction 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 CHEMISTRYIntroductionSynthesis of a-Acidic IsocyanidesReactivity of a-Acidic IsocyanidesMCRs Involving a-Acidic IsocyanidesConclusions 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 ProofUGI AND PASSERINI REACTIONS WITH CARBOXYLIC ACID SURROGATESIntroductionCarboxylic Acid SurrogatesUse of Mineral and Lewis AcidsConclusionsAMINE (IMINE) COMPONENT SURROGATES IN THE UGI REACTION AND RELATED ISOCYANIDE-BASED MULTICOMPONENT REACTIONS Introduction Hydroxylamine Components in the Ugi ReactionHydrazine Components in the Ugi Reaction Miscellaneous Amine Surrogates for the Ugi ReactionActivated 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 IsocyanoacetatesSynthesis of Porphyrins and Related Compounds ConclusionISOCYANIDE-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 4Imidazoles Pyrazoles Oxadiazoles and TriazolesTetrazoles Benzofurans and Benzimidazoles Indoles Quinolines Quinoxaline RENAISSANCE OF ISOCYANOARENES AS LIGANDS IN LOW-VALENT ORGANOMETALLICS Historical PerspectiveIsocyanidemetalates 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 AmidineIntramolecular Cyclizations of Functionalized Isocyanide Ligands Coupling of Isocyanides with DipolesOther Reactions Final Remarks POLYISOCYANIDES IntroductionThe Polymerization Mechanism Conformation of the Polymeric Backbone Polyisocyanopeptides Polyisocyanides as Scaffolds for the Anchoring of Chromophoric Molecules Functional Polyisocyanides Conclusions and Outlook

Info autore

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.

Riassunto

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.

Dettagli sul prodotto

• Autori: V. Nenajdenko
• Con la collaborazione di: Nenajdenko (Editore), V Nenajdenko (Editore), V. Nenajdenko (Editore), Valentine Nenajdenko (Editore)
• Editore: Wiley-VCH
• Lingue: Inglese, Tedesco
• Formato: Copertina rigida
• Pubblicazione: 01.07.2012
• EAN: 9783527330430
• ISBN: 978-3-527-33043-0
• Pagine: 606
• Dimensioni: 173 mm x 245 mm x 33 mm
• Peso: 1278 g
• Illustrazioni: 712 SW-Abb., 30 Tabellen
• Categorie: Scienze naturali, medicina, informatica, tecnica > Chimica > Chimica organica; Chemie, Organische Chemie, chemistry, Organische Synthese, Natural Products, Naturstoffchemie, Pharmaceutical & Medicinal Chemistry, Pharmazeutische u. Medizinische Chemie, Methods - Synthesis & Techniques, Organische Chemie / Methoden, Synthesen, Verfahren