Microwaves in Organic and Medicinal Chemistry -- Contents -- Preface -- Personal Foreword to the First Edition -- Personal Foreword to the Second Edition -- 1 Introduction: Microwave Synthesis in Perspective -- 1.1 Microwave Synthesis and Medicinal Chemistry -- 1.2 Microwave-Assisted Organic Synthesis (MAOS): A Brief History -- 1.3 Scope and Organization of the Book -- References -- 2 Microwave Theory -- 2.1 Microwave Radiation -- 2.2 Microwave Dielectric Heating -- 2.3 Dielectric Properties -- 2.4 Microwave versus Conventional Thermal Heating -- 2.5 Microwave Effects -- 2.5.1 Temperature Monitoring in Microwave Chemistry -- 2.5.2 Thermal Effects (Kinetics) -- 2.5.3 Specific Microwave Effects -- 2.5.4 Nonthermal (Athermal) Microwave Effects -- References -- 3 Equipment Review -- 3.1 Introduction -- 3.2 Domestic Microwave Ovens -- 3.3 Dedicated Microwave Reactors for Organic Synthesis -- 3.4 Single-Mode Instruments -- 3.4.1 Anton Paar GmbH -- 3.4.1.1 Monowave 300 -- 3.4.2 Biotage AB -- 3.4.2.1 Initiator Platform -- 3.4.2.2 Chemspeed SWAVE -- 3.4.2.3 Peptide Synthesizers -- 3.4.3 CEM Corporation -- 3.4.3.1 Discover Platform -- 3.4.3.2 Explorer Systems -- 3.4.3.3 Voyager System -- 3.4.3.4 Peptide Synthesizers -- 3.5 Multimode Instruments -- 3.5.1 Anton Paar GmbH -- 3.5.1.1 Synthos 3000 -- 3.5.1.2 Masterwave Benchtop Reactor -- 3.5.2 Biotage AB -- 3.5.3 CEM Corporation -- 3.5.3.1 MARS Scale-Up System Accessories -- 3.5.3.2 MARS Parallel System Accessories -- 3.5.4 Milestone s.r.l -- 3.5.4.1 MultiSYNTH System -- 3.5.4.2 MicroSYNTH Labstation -- 3.5.4.3 StartSYNTH -- 3.5.4.4 Scale-Up Systems -- 3.5.4.5 Microwave-Heated Autoclave Systems -- References -- 4 Microwave Processing Techniques -- 4.1 Solvent-Free Reactions -- 4.2 Phase-Transfer Catalysis -- 4.3 Open- versus Closed-Vessel Conditions -- 4.4 Pre-pressurized Reaction Vessels.

4.5 Nonclassical Solvents -- 4.5.1 Water as Solvent -- 4.5.2 Ionic Liquids -- 4.6 Passive Heating Elements -- 4.7 Processing Techniques in Drug Discovery and High-Throughput Synthesis -- 4.7.1 Automated Sequential versus Parallel Processing -- 4.7.2 High-Throughput Synthesis Methods -- 4.7.2.1 Solid-Phase Synthesis -- 4.7.2.2 Soluble Polymer-Supported Synthesis -- 4.7.2.3 Fluorous-Phase Organic Synthesis -- 4.7.2.4 Polymer-Supported Reagents, Catalysts, and Scavengers -- 4.8 Scale-Up in Batch and Continuous Flow -- 4.8.1 Scale-Up in Batch and Parallel -- 4.8.2 Scale-Up Using Continuous Flow Techniques -- 4.8.3 Scale-Up Using Stop-Flow Techniques -- 4.8.4 Microwave Reactor Systems for Production Scale -- References -- 5 Literature Survey Part A: Transition Metal-Catalyzed Reactions -- 5.1 General Comments -- 5.2 Carbon-Carbon Bond Formations -- 5.2.1 Heck Reactions -- 5.2.2 Suzuki-Miyaura Reactions -- 5.2.3 Sonogashira Reactions -- 5.2.4 Stille Reactions -- 5.2.5 Negishi, Kumada, and Related Reactions -- 5.2.6 Carbonylation Reactions -- 5.2.7 Asymmetric Allylic Alkylations -- 5.2.8 Miscellaneous Carbon-Carbon Bond-Forming Reactions -- 5.3 Carbon-Heteroatom Bond Formations -- 5.3.1 Buchwald-Hartwig Reactions -- 5.3.2 Ullmann Condensation Reactions -- 5.3.3 Miscellaneous Carbon-Heteroatom Bond-Forming Reactions -- 5.4 Other Transition Metal-Mediated Processes -- 5.4.1 Ring-Closing Metathesis and Cross-Metathesis -- 5.4.2 Pauson-Khand Reactions -- 5.4.3 Carbon-Hydrogen Bond Activation -- 5.4.4 Copper-Catalyzed Azide-Acetylene Cycloaddition (CuAAC) -- 5.4.5 Miscellaneous Reactions -- References -- 6 Literature Survey Part B: Miscellaneous Organic Transformations -- 6.1 Rearrangement Reactions -- 6.1.1 Claisen Rearrangements -- 6.1.2 Domino/Tandem Claisen Rearrangements -- 6.1.3 Squaric Acid-Vinylketene Rearrangements.

6.1.4 Vinylcyclobutane-Cyclohexene Rearrangements -- 6.1.5 Miscellaneous Rearrangements -- 6.2 Cycloaddition Reactions -- 6.2.1 Diels-Alder Reactions -- 6.2.2 Miscellaneous Cycloadditions -- 6.3 Oxidations -- 6.4 Reductions and Hydrogenations -- 6.5 Mitsunobu Reactions -- 6.6 Glycosylation Reactions and Related Carbohydrate-Based Transformations -- 6.7 Organocatalytic Transformations -- 6.8 Organometallic Transformations (Mg, Zn, and Ti) -- 6.9 Multicomponent Reactions -- 6.10 Alkylation Reactions -- 6.11 Nucleophilic Aromatic Substitutions -- 6.12 Ring-Opening Reactions -- 6.12.1 Cyclopropane and Cyclobutene Ring Openings -- 6.12.2 Aziridine Ring Openings -- 6.12.3 Epoxide Ring Openings -- 6.13 Addition and Elimination Reactions -- 6.13.1 Michael Additions -- 6.13.2 Addition to Alkynes -- 6.13.3 Addition to Alkenes -- 6.13.4 Addition to Nitriles -- 6.13.5 Elimination Reactions -- 6.14 Substitution Reactions -- 6.15 Enamine and Imine Formations -- 6.16 Reductive Aminations -- 6.17 Ester and Amide Formation -- 6.18 Decarboxylation Reactions -- 6.19 Free Radical Reactions -- 6.20 Protection/Deprotection Chemistry -- 6.21 Preparation of Isotopically Labeled Compounds -- 6.22 Miscellaneous Transformations -- References -- 7 Literature Survey Part C: Heterocycle Synthesis -- 7.1 Three-Membered Heterocycles with One Heteroatom -- 7.2 Four-Membered Heterocycles with One Heteroatom -- 7.3 Five-Membered Heterocycles with One Heteroatom -- 7.3.1 Pyrroles -- 7.3.2 Furans -- 7.3.3 Thiophenes -- 7.4 Five-Membered Heterocycles with Two Heteroatoms -- 7.4.1 Pyrazoles -- 7.4.2 Imidazoles -- 7.4.3 Isoxazoles -- 7.4.4 Oxazoles -- 7.4.5 Thiazoles -- 7.5 Five-Membered Heterocycles with Three Heteroatoms -- 7.5.1 1,2,3-Triazoles -- 7.5.2 1,2,4-Triazoles -- 7.5.3 1,2,4-Oxadiazoles -- 7.5.4 1,3,4-Oxadiazoles -- 7.5.5 1,3,2-Diazaphospholidines.

7.6 Five-Membered Heterocycles with Four Heteroatoms -- 7.7 Six-Membered Heterocycles with One Heteroatom -- 7.7.1 Piperidines -- 7.7.2 Pyridines -- 7.7.3 Pyrans -- 7.8 Six-Membered Heterocycles with Two Heteroatoms -- 7.8.1 Pyrimidines -- 7.8.2 Pyrazines -- 7.8.3 Pyridazines -- 7.8.4 Oxazines -- 7.8.5 Thiazines -- 7.9 Six-Membered Heterocycles with Three Heteroatoms -- 7.10 Larger Heterocyclic and Polycyclic Ring Systems -- References -- 8 Literature Survey Part D: Combinatorial Chemistry and High-Throughput Organic Synthesis -- 8.1 Solid-Phase Organic Synthesis -- 8.1.1 Peptide Synthesis and Related Examples -- 8.1.2 Resin Functionalization -- 8.1.3 Transition Metal Catalysis -- 8.1.4 Substitution Reactions -- 8.1.5 Multicomponent Chemistry -- 8.1.6 Condensation Reactions -- 8.1.7 Rearrangements -- 8.1.8 Cleavage Reactions -- 8.1.9 Miscellaneous -- 8.2 Soluble Polymer-Supported Synthesis -- 8.3 Fluorous-Phase Organic Synthesis -- 8.4 Grafted Ionic Liquid-Phase-Supported Synthesis -- 8.5 Polymer-Supported Reagents -- 8.6 Polymer-Supported Catalysts -- 8.6.1 Catalysts on Polymeric Support -- 8.6.2 Silica-Grafted Catalysts -- 8.6.3 Catalysts Immobilized on Glass -- 8.6.4 Catalysts Immobilized on Carbon -- 8.6.5 Miscellaneous -- 8.7 Polymer-Supported Scavengers -- References -- Index.