Multicomponent reactions in organic synthesis
Comprehensive and up-to-date, this book focuses on the latest advances in the field, such as newly developed techniques, more environmentally benign processes, broadened scopes, and completely novel MCRs. In addition to carbene-promoted MCRs and frequently applied metal-catalyzed MCRs, it also cover...
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| Main Authors | , , |
|---|---|
| Format | eBook Book |
| Language | English |
| Published |
Weinheim
Wiley-VCH
2015
Wiley John Wiley & Sons, Incorporated |
| Edition | 1 |
| Subjects | |
| Online Access | Get full text |
| ISBN | 3527332375 9783527332373 3527678204 9783527678204 |
| DOI | 10.1002/9783527678174 |
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| Abstract | Comprehensive and up-to-date, this book focuses on the latest advances in the field, such as newly developed techniques, more environmentally benign processes, broadened scopes, and completely novel MCRs. In addition to carbene-promoted MCRs and frequently applied metal-catalyzed MCRs, it also covers recently developed catalytic enantioselective variants as well as MCR in drug discovery and for the synthesis of heterocyclic molecules and macrocycles. Edited by the leading experts and with a list of authors reading like a "who's who" in multicomponent reaction chemistry, this is definitely a must-have for every synthetic organic chemist as well as medicinal chemists working in academia and pharmaceutical companies. |
|---|---|
| AbstractList | Comprehensive and up-to-date, this book focuses on the latest advances in the field, such as newly developed techniques, more environmentally benign processes, broadened scopes, and completely novel MCRs. In addition to carbene-promoted MCRs and frequently applied metal-catalyzed MCRs, it also covers recently developed catalytic enantioselective variants as well as MCR in drug discovery and for the synthesis of heterocyclic molecules and macrocycles. Edited by the leading experts and with a list of authors reading like a "who's who" in multicomponent reaction chemistry, this is definitely a must-have for every synthetic organic chemist as well as medicinal chemists working in academia and pharmaceutical companies. |
| Author | Wang, Qian Wang, Mei-Xiang Zhu, Jieping |
| Author_xml | – sequence: 1 fullname: Zhu, Jieping – sequence: 2 fullname: Wang, Qian – sequence: 3 fullname: Wang, Mei-Xiang |
| BackLink | https://cir.nii.ac.jp/crid/1130282271120268288$$DView record in CiNii |
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| Notes | Includes bibliographical references and index |
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| PublicationPlace | Weinheim |
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| Publisher | Wiley-VCH Wiley John Wiley & Sons, Incorporated |
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| Snippet | Comprehensive and up-to-date, this book focuses on the latest advances in the field, such as newly developed techniques, more environmentally benign processes,... |
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| SubjectTerms | Chemical reactions Organic compounds Organic compounds -- Synthesis |
| TableOfContents | Multicomponent Reactions in Organic Synthesis -- Contents -- List of Contributors -- Preface -- 1. General Introduction to MCRs: Past, Present, and Future -- 1.1 Introduction -- 1.2 Advances in Chemistry -- 1.3 Total Syntheses -- 1.4 Applications in Pharmaceutical and Agrochemical Industry -- 1.5 Materials -- 1.6 Outlook -- References -- 2. Discovery of MCRs -- 2.1 General Introduction -- 2.2 The Concept -- 2.3 The Reaction Design Concept -- 2.3.1 Single Reactant Replacement -- 2.3.2 Modular Reaction Sequences -- 2.3.3 Condition-Based Divergence -- 2.3.4 Union of MCRs -- 2.4 Multicomponent Reactions and Biocatalysis -- 2.4.1 Multicomponent Reactions and (Dynamic) Enzymatic Kinetic Resolution -- 2.4.2 Multicomponent Reactions and Enzymatic Desymmetrization -- 2.5 Multicomponent Reactions in Green Pharmaceutical Production -- 2.6 Conclusions -- Acknowledgments -- References -- 3. Aryne-Based Multicomponent Reactions -- 3.1 Introduction -- 3.2 Multicomponent Reactions of Arynes via Electrophilic Coupling -- 3.2.1 Multicomponent Reactions under Neutral Conditions -- 3.2.1.1 Isocyanide-Based Multicomponent Reactions -- 3.2.1.2 Imine-Based Multicomponent Reactions -- 3.2.1.3 Amine-Based Multicomponent Reactions -- 3.2.1.4 Carbonyl Compound-Based Multicomponent Reactions -- 3.2.1.5 Ether-Based Multicomponent Reactions -- 3.2.1.6 Miscellaneous -- 3.2.2 Multicomponent Reactions under Basic Conditions -- 3.3 Transition Metal-Catalyzed Multicomponent Reactions of Arynes -- 3.3.1 Annulations -- 3.3.2 Cross-Coupling-Type Reactions -- 3.3.3 Mizoroki-Heck-Type Reactions -- 3.3.4 Insertion into σ-Bond -- 3.4 Concluding Remarks -- References -- 4. Ugi-Smiles and Passerini-Smiles Couplings -- 4.1 Introduction -- 4.1.1 Carboxylic Acid Surrogates in Ugi Reactions -- 4.1.2 Smiles Rearrangements -- 4.2 Scope and Limitations -- 4.2.1 Phenols and Thiophenols 7.3.2 Asymmetric Examples -- 7.3.2.1 Chiral Reagent Induction -- 7.3.2.2 Chiral Dirhodium(II) Catalysis -- 7.3.2.3 Enantioselective Synergistic Catalysis -- 7.3.3 MCRs Followed by Tandem Cyclizations -- 7.4 MCRs via Electrophilic Trapping of Zwitterionic Intermediates -- 7.5 MCRs via Metal Carbene Migratory Insertion -- 7.6 Summary and Outlook -- References -- 8. Metal-Catalyzed Multicomponent Synthesis of Heterocycles -- 8.1 Introduction -- 8.2 Multicomponent Cross-Coupling and Carbonylation Reactions -- 8.2.1 Cyclization with Alkyne- or Alkene-Containing Nucleophiles -- 8.2.2 Cyclization via Palladium-Allyl Complexes -- 8.2.3 Fused-Ring Heterocycles for ortho-Substituted Arene Building Blocks -- 8.2.4 Multicomponent Cyclocarbonylations -- 8.2.5 Cyclization of Cross-Coupling Reaction Products -- 8.2.6 C‒H Functionalization in Multicomponent Reactions -- 8.3 Metallacycles in Multicomponent Reactions -- 8.4 Multicomponent Reactions via 1,3-Dipolar Cycloaddition -- 8.5 Concluding Remarks -- References -- 9. Macrocycles from Multicomponent Reactions -- 9.1 Introduction -- 9.2 IMCR-Based Macrocyclizations of Single Bifunctional Building Blocks -- 9.3 Multiple MCR-Based Macrocyclizations of Bifunctional Building Blocks -- 9.4 IMCR-Based Macrocyclizations of Trifunctionalized Building Blocks (MiB-3D) -- 9.5 Sequential IMCR-Based Macrocyclizations of Multiple Bifunctional Building Blocks -- 9.6 Final Remarks and Future Perspectives -- References -- 10. Multicomponent Reactions under Oxidative Conditions -- 10.1 Introduction -- 10.2 Multicomponent Reactions Involving In Situ Oxidation of One Substrate -- 10.2.1 Isocyanide-Based Multicomponent Reactions -- 10.2.1.1 Passerini Reactions -- 10.2.1.2 Ugi Reactions with In Situ Oxidation of Alcohols -- 10.2.1.3 Ugi Reaction with In Situ Oxidation of Secondary Amines Acknowledgment -- References -- 13. Anhydride-Based Multicomponent Reactions -- 13.1 Introduction -- 13.2 Quinolones and Related Heterocycles from Homophthalic and Isatoic Anhydrides -- 13.2.1 Introduction: Reactivity of Homophthalic and Isatoic Anhydrides -- 13.2.2 Imine-Anhydride Reactions of Homophthalic Anhydride -- 13.2.3 MCRs Employing Homophthalic Anhydride -- 13.2.4 Imine-Anhydride Reactions of Isatoic Anhydride -- 13.3 α,β-Unsaturated Cyclic Anhydrides: MCRs Involving Conjugate Addition and Cycloaddition Reactions -- 13.3.1 Maleic Anhydride MCRs -- 13.3.2 MCRs of Itaconic Anhydrides -- 13.3.3 Diels-Alder Reactions -- 13.4 MCRs of Cyclic Anhydrides in Annulation Reactions and Related Processes -- 13.4.1 MCR-Based Annulations: Succinic and Phthalic Anhydrides -- 13.5 MCRs of Acyclic Anhydrides -- 13.6 Conclusions -- References -- 14. Free-Radical Multicomponent Processes -- 14.1 Introduction -- 14.2 MCRs Involving Addition Across Olefin C=C Bonds -- 14.2.1 Addition of Aryl Radicals to Olefins -- 14.2.2 MCRs Using Sulfonyl Derivatives as Terminal Trap -- 14.2.3 Carboallylation of Electron-Poor Olefins -- 14.2.4 Carbohydroxylation, Sulfenylation, and Phosphorylation of Olefins -- 14.2.5 Radical Addition to Olefins Using Photoredox Catalysis -- 14.2.6 MCRs Based on Radical-Polar Crossover Processes -- 14.3 Free-Radical Carbonylation -- 14.3.1 Alkyl Halide Carbonylation -- 14.3.2 Metal-Mediated Atom-Transfer Radical Carbonylation -- 14.3.3 Alkane Carbonylation -- 14.3.4 Miscellaneous Carbonylation Reactions -- 14.4 Free-Radical Oxygenation -- 14.5 MCRs Involving Addition Across π-C=N Bonds -- 14.5.1 Free-Radical Strecker Process -- 14.5.2 Free-Radical Mannich-Type Processes -- 14.6 Miscellaneous Free-Radical Multicomponent Reactions -- 14.7 Conclusions -- References -- 15. Chiral Phosphoric Acid-Catalyzed Asymmetric Multicomponent Reactions 15.1 Introduction 10.2.1.4 Ugi-Smiles Reaction with In Situ Oxidation of Secondary Amines -- 10.2.1.5 Ugi-Type Reactions by In Situ Oxidation of Tertiary Amines -- 10.2.1.6 Synthesis of Other Derivatives -- 10.2.2 Other Multicomponent Reactions -- 10.3 Multicomponent Reactions Involving Oxidation of a Reaction Intermediate -- 10.3.1 Reactions without Transition Metal-Mediated Oxidation -- 10.3.2 Reactions Mediated by Transition Metal Catalysis -- 10.4 Multicomponent Reactions Involving Oxidants as Lewis Acids -- 10.5 Conclusions -- References -- 11. Allenes in Multicomponent Synthesis of Heterocycles -- 11.1 Introduction -- 11.2 Reactions with 1,2-Propadiene and Unactivated Allenes -- 11.2.1 Palladium-Catalyzed Multicomponent Reactions -- 11.2.2 Copper-, Nickel-, and Rhodium-Promoted Multicomponent Reactions -- 11.2.3 Multicomponent Reactions without Transition Metals -- 11.3 Reactions with Acceptor-Substituted Allenes -- 11.3.1 Catalyzed Multicomponent Reactions -- 11.3.2 Uncatalyzed Multicomponent Reactions -- 11.4 Reactions with Donor-Substituted Allenes -- 11.5 Conclusions -- List of Abbreviations -- References -- 12. Alkynes in Multicomponent Synthesis of Heterocycles -- 12.1 Introduction -- 12.2 σ-Nucleophilic Reactivity of Alkynes -- 12.2.1 Acetylide Additions to Electrophiles -- 12.2.1.1 Alkyne-Aldehyde-Amine Condensation - A-Coupling -- 12.2.1.2 Alkyne-(Hetero)Aryl Halide (Sonogashira) Coupling as Key Reaction -- 12.2.2 Conversion of Terminal Alkynes into Electrophiles as Key Reactions -- 12.3 π-Nucleophilic Reactivity of Alkynes -- 12.4 Alkynes as Electrophilic Partners -- 12.5 Alkynes in Cycloadditions -- 12.5.1 Alkynes as Dipolarophiles -- 12.5.2 Alkynes in Cu(I)-Catalyzed 1,3-Dipolar Azide-Alkyne Cycloaddition -- 12.5.3 Alkynes as Dienophiles in MCRs -- 12.6 Alkynes as Reaction Partners in Organometallic MCRs -- 12.7 Conclusions -- List of Abbreviations 4.2.2 Six-Membered Ring Hydroxy Heteroaromatics and Related Mercaptans -- 4.2.3 Five-Membered Ring Hydroxy Heteroaromatic and Related Mercaptans -- 4.2.4 Related Couplings with Enol Derivatives -- 4.2.5 The Joullié-Smiles Coupling -- 4.2.6 The Passerini-Smiles Reaction -- 4.3 Ugi-Smiles Postcondensations -- 4.3.1 Postcondensations Involving Reduction of the Nitro Group -- 4.3.2 Transformations of Ugi-Smiles Thioamides -- 4.3.3 Postcondensations Involving Transition Metal-Catalyzed Processes -- 4.3.4 Reactivity of the Peptidyl Unit -- 4.3.5 Radical Reactions -- 4.3.6 Cycloaddition -- 4.4 Conclusions -- References -- 5. 1,3-Dicarbonyls in Multicomponent Reactions -- 5.1 Introduction -- 5.2 Achiral and Racemic MCRs -- 5.2.1 Involving One Pronucleophilic Reactive Site -- 5.2.2 Involving Two Reactive Sites -- 5.2.2.1 Two Nucleophilic Sites -- 5.2.2.2 One Pronucleophilic Site and One Electrophilic Site -- 5.2.3 Involving Three Reactive Sites -- 5.2.4 Involving Four Reactive Sites -- 5.3 Enantioselective MCRs -- 5.3.1 Involving One Reactive Site -- 5.3.2 Involving Two Reactive Sites -- 5.3.3 Involving Three Reactive Sites -- 5.4 Conclusions and Outlook -- References -- 6. Functionalization of Heterocycles by MCRs -- 6.1 Introduction -- 6.2 Mannich-Type Reactions and Related Processes -- 6.3 β-Dicarbonyl Chemistry -- 6.4 Hetero-Diels-Alder Cycloadditions and Related Processes -- 6.5 Metal-Mediated Processes -- 6.6 Isocyanide-Based Reactions -- 6.7 Dipole-Mediated Processes -- 6.8 Conclusions -- Acknowledgments -- References -- 7. Diazoacetate and Related Metal-Stabilized Carbene Species in MCRs -- 7.1 Introduction -- 7.2 MCRs via Carbonyl or Azomethine Ylide-Involved 1,3-Dipolar Cycloadditions -- 7.2.1 Azomethine Ylide -- 7.2.2 Carbonyl Ylide -- 7.3 MCRs via Electrophilic Trapping of Protic Onium Ylides -- 7.3.1 Initial Development |
| Title | Multicomponent reactions in organic synthesis |
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