Multicomponent Reactions in Organic Synthesis

Preface

GENERAL INTRODUCTION TO MCRs: PAST, PRESENT, AND FUTURE
Introduction
Advances in Chemistry
Total Synthesis
Applications in Pharmaceutical and Agrochemical Industry
Materials
Outlook

DISCOVERY OF MCRs
General Introduction
The Concept
The Reaction Design Concept
Multicomponent Reactions and Biocatalysis
Multicomponent Reactions in Green Pharmaceutical Production
Conclusions

ARYNE-BASED MULTICOMPONENT REACTIONS
Introduction
Multicomponent Reactions of Arynes via Electrophilic Coupling
Transition Metal-Catalyzed Multicomponent Reactions of Arynes
Concluding Remarks

UGI-SMILES AND PASSERINI-SMILES COUPLINGS
Introduction
Scope and Limitations
Ugi-Smiles Postcondensations
Conclusions

1,3-DICARBONYLS IN MULTICOMPONENT REACTIONS
Introduction
Achiral and Racemic MCRs
Enantioselective MCRs
Conclusions and Outlook

FUNCTIONALIZATION OF HETEROCYCLES BY MCRs
Introduction
Mannich-Type Reactions and Related Processes
Beta-Dicarbonyl Chemistry
Hetero-Diels-Alder Cycloadditions and Related Processes
Metal-Mediated Processes
Isocyanide-Based Reactions
Dipole-Mediated Processes
Conclusions

DIAZOACETATE AND RELATED METAL-STABILIZED CARBENE SPECIES IN MCRs
Introduction
MCRs via Carbonyl or Azomethine Ylide-Involved 1,3-Dipolar Cycloadditions
MCRs via Electrophilic Trapping of Protic Onium Ylides
MCRs via Electrophilic Trapping of Zwitterionic Intermediates
MCRs via Metal Carbene Migratory Insertion
Summary and Outlook

METAL-CATALYZED MULTICOMPONENT SYNTHESIS OF HETEROCYCLES
Introduction
Multicomponent Cross-Coupling and Carbonylation Reactions
Metallacycles in Multicomponent Reactions
Multicomponent Reactions via 1,3-Dipolar Cycloaddition
Concluding Remarks

MACROCYCLES FROM MULTICOMPONENT REACTIONS
Introduction
IMCR-Based Macrocyclizations of Single Bifunctional Building Blocks
Multiple MCR-Based Macrocyclizations of Bifunctional Building Blocks
IMCR-Based Macrocyclizations of Trifunctionalized Building Blocks (MiB-3D)
Sequential IMCR-Based Macrocyclizations of Multiple Bifunctional Building Blocks
Final Remarks and Future Perpectives

MULTICOMPONENT REACTIONS UNDER OXIDATIVE CONDITIONS
Introduction
Multicomponent Reactions Involving In-Situ Oxidation of One Substrate
Multicomponent Reactions Involving Oxidation of a Reaction Intermediate
Multicomponent Reactions Involving Oxidants as Lewis Acids
Conclusions

ALLENES IN MULTICOMPONENT SYNTHESIS OF HETEROCYCLES
Introduction
Reactions with 1,2-Propadiene and Unactivated Allenes
Reactions with Acceptor-Substituted Allenes
Reactions with Donor-Substituted Allenes
Conclusions

ALKYNES IN MULTICOMPONENT SYNTHESIS OF HETEROCYCLES
Introduction
Sigma-Nucleophilic Reactivity of Alkynes
Pi-Nucleophilic Reactivity of Alkynes
Alkynes as Electrophilic Partners
Alkynes in Cycloadditions
Alkynes as Reaction Partners in Organometallic MCRs
Conclusions

ANHYDRIDE-BASED MULTICOMPONENT REACTIONS
Introduction
Quinolones and Related Heterocylces from Homophthalic and Isatoic Anhydrides
Alpha, Beta-Unsaturated Cyclic Anhydrides: MCRs Involving Conjugate Addition and Cycloaddition Reactions
MCRs of Cyclic Anhydrides in Annulation Reactions and Related Processes
MRCs of Acyclic Anhydrides
Conclusions

FREE-RADICAL MULTICOMPONENT PROCESSES
Introduction
MCRs Involving Addition Across Olefin C=C Bonds
Free-Radical Carbonylation
Free-Radical Oxygenation
MCRs Involving Addition Across Pi-C=N Bonds
Miscellaneous Free-Radical Multicomponent Reactions
Conclusions

CHIRAL PHOSPHORIC ACID-CATALYZED ASYMMETRIC MULTICOMPONENT REACTIONS
Introduction
Mannich Reaction
Ugi-Type Reaction
Biginelli Reaction
Aza-Diels-Alder Reaction
1,3-Dipolar Cycloaddition
Hantzsch Dihydropyridine Synthesis
The Combination of Metal and Chiral Phosphoric Acid for Multicomponent Reaction
Other Phosphoric Acid-Catalyzed Multicomponent Reactions
Summary

Index