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Microwaves in Organic and Medicinal Chemistry

by

Microwaves in Organic and Medicinal Chemistry Cover

 

Synopses & Reviews

Publisher Comments:

The complete guide to microwave synthesis in medicinal chemistry synthesis — while also containing a "crash-course" for newcomers.

Compared to conventional heating methods, microwave irradiation causes less side-reactions and losses through decomposition and can be easily adapted to different chemical reaction conditions. Cheap and reliable, this method has been successfully used for a variety of chemical reactions, most notably in the synthesis of drugs and drug-like compounds.

In this handy reference, the authors focus on common reaction types in medicinal chemistry, including solid-phase and combinatorial methods. They consider the underlying theory, latest developments in microwave applications and include a variety of examples from recent literature, as well as less common applications that are equally relevant for organic and medicinal chemists.

From the contents:

  • Introduction
  • Microwave theory
  • Equipment review
  • Microwave processing techniques
  • Getting started with microwave chemistry
  • Literature survey: general organic synthesis
  • Literature survey: combinatorial and high-throughput synthesis

The authors are all experts on the use of microwaves for drug synthesis and have ample teaching experience from courses held under the auspices of the American Chemical Society and the IUPAC. The result is an indispensable information source for organic and medicinal chemists, as well as those in industry and the pharmaceutical industry.

Book News Annotation:

Indispensable in the kitchen, and now in the chemistry lab, microwaves differ from conventional heating methods and open new possibilities for synthesis in the hands of those who have the necessary education in this technology. Pharmaceutical research in particular can benefit from the speeded up chemical reactions and the libraries of purified single compounds that can be created. The authors begin with the fundamentals—the history of microwave-assisted organic synthesis, and the various aspects of microwave theory. Following is a detailed equipment review and then discussion of techniques and of how to get started. The final sections survey the literature, first on general organic synthesis and then on combinatorial chemistry and high-throughput organic synthesis.
Annotation 2005 Book News, Inc., Portland, OR (booknews.com)

Book News Annotation:

Indispensable in the kitchen, and now in the chemistry lab, microwaves differ from conventional heating methods and open new possibilities for synthesis in the hands of those who have the necessary education in this technology. Pharmaceutical research in particular can benefit from the speeded up chemical reactions and the libraries of purified single compounds that can be created. The authors begin with the fundamentals—the history of microwave-assisted organic synthesis, and the various aspects of microwave theory. Following is a detailed equipment review and then discussion of techniques and of how to get started. The final sections survey the literature, first on general organic synthesis and then on combinatorial chemistry and high-throughput organic synthesis. Annotation ©2005 Book News, Inc., Portland, OR (booknews.com)

Synopsis:

The authors of this guide are experts on the use of microwaves for drug synthesis as well as having much experience in teaching courses held under the auspices of the American Chemical Society and the IUPAC.

In this handy source of information for any practicing synthetic chemist they focus on common reaction types in medicinal chemistry, including solid-phase and combinatorial methods. They consider the underlying theory, latest developments in microwave applications and include a variety of examples from recent literature, as well as less common applications that are equally relevant for organic and medicinal chemists.

An indispensable reference for researchers with an affinity to modern methods.

Synopsis:

A handy guide for organic and medicinal chemists focusing on common reaction types in medicinal chemistry, including solid-phase and combinatorial methods. Microwave theory, latest developments in instrumentation and a variety of examples from the recent literature are included.

About the Author

C. Oliver Kappe was born in Graz (Austria) and received his doctoral degree from the Karl-Franzens-University in Graz in 1992, working with Gert Kollenz on acylketenes. After postdoctoral research work with Curt Wentrup at the University of Queensland, Brisbane (Australia), and with Albert Padwa at Emory University, Atlanta (USA), he moved back to the University of Graz where he currently holds a position as associate Professor. In 2003 he spent a sabbatical at the Scripps Research Institute in La Jolla (USA) with K. Barry Sharpless. His research focuses on microwave-enhanced synthesis, combinatorial chemistry, multicomponent reactions, and biologically active heterocycles.

Alexander Stadler was born in Bruck and der Mur (Austria) and studied Chemistry at the University of Graz. He then obtained his doctoral degree for studies on microwave-accelerated reactions in solution and on solid phase in the group of C. Oliver Kappe. After postdoctoral research work on microwave-assisted transition metal-catalyzed coupling reactions in the group of Mats Larhed at the University of Uppsala (Sweden) he joined Anton Paar GmbH in Graz in 2004 as product specialist for microwave synthesis.

Table of Contents

Preface.

Personal Foreword.

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.

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 Thermal Effects (Kinetics).

2.5.2 Specific Microwave Effects.

2.5.3 Non-Thermal (Athermal) Microwave Effects.

3. Equipment Review.

3.1 Introduction.

3.2 Domestic Microwave Ovens.

3.3 Dedicated Microwave Reactors for Organic Synthesis.

3.4 Multimode Instruments.

3.4.1 Milestone s.r.1.

3.4.2 CEM Corporation.

3.4.3 Biotage AB.

3.4.4 Anton Paar GmbH.

3.5 Single-Model Instruments.

3.5.1 Biotage AB.

3.5.2 CEM Corporation.

3.6 Discussion.

4. Microwave Processing Techniques.

4.1 Solvent-Free Reactions.

4.2 Phase-Transfer Catalysis.

4.3 Reactions Using Solvents.

4.3.1 Open-versus Closed-Vessel Conditions.

4.3.2 Pre-Pressurized Reaction Vessels.

4.3.3 Non-Classical Solvents.

4.4 Parallel Processing.

4.5 Scale-Up in Batch and Continuous-Flow.

5. Starting with Microwave Chemistry.

5.1 Why Use Microwave Reactors?

5.2 Translating Conventionally Heated Methods.

5.2.1 Open and Closed Vessels?

5.2.2 Choice of Solvent.

5.2.3 Temperature and Time.

5.2.4 Microwave Instrument Software.

5.3 Reaction Optimization and Library Generation – A Case Study.

5.3.1 Choice of Solvent.

5.3.2 Catalyst Selection.

5.3.3 Time and Temperature.

5.3.4 Reinvestigation by a “Design of Experiments” Approach.

5.3.5 Optimization for Troublesome Building Block Combinations.

5.3.6 Automated Sequential Library Production.

5.4 Limitations and Safety Aspects.

6. Literature Survey Part A: General Organic Synthesis.

6.1 Transition Metal-Catalyzed Carbon-Carbon Bond Formations.

6.1.1 Heck Reactions.

6.1.2 Suzuki Reactions.

6.1.3 Sonogashira Reactions.

6.1.4 Stille Reactions.

6.1.5 Negishi, Kumada, and Related Reactions.

6.1.6 Carbonylation Reactions.

6.1.7 Asymmetric Allylic Alkyations.

6.1.8 Miscellaneous Carbon-Carbon Bond-Forming Reactions.

6.2 Transition Metal-Catalyzed Carbon-Heteroatom Bond Formations.

6.2.1 Buchwald-Hartwig Reactions.

6.2.2 Ullmann Condensation Reactions.

6.2.3 Miscellaneous Carbon-Heteroatom Bond-Forming Reactions.

6.3 Other Transition Metal-Mediated Processes.

6.3.1 Ring Closing Metathesis.

6.3.2 Pauson-Khand Reactions.

6.3.3 Carbon-Hydrogen Bond Activation.

6.3.4 Miscellaneous Reactions.

6.4 Rearrangement Reactions.

6.4.1 Claisen Rearrangements.

6.4.2 Domino/Tandem Claisen Rearrangements.

6.4.3 Squaric Acid-Vinylketene Rearrangements.

6.4.4 Vinylcyclobutane-Cyclohexene Rearrangements.

6.4.5 Miscellaneous Rearrangements.

6.5 Diels-Alder Cycloaddition Reactions.

6.6 Oxidations.

6.7 Catalytic Transfer Hydrogenations.

6.8 Mitsunobu Reactions.

6.9 Glycosylation Reactions and Related Carbohydrate-Based Transformations.

6.10 Multicomponent Reactions.

6.11 Alkylation Reactions.

6.12 Nucleophilic Aromatic Substitutions.

6.13 Ring-Opening Reactions.

6.13.1 Cyclopropane Ring-Opening.

6.13.2 Aziridine Ring-Openings.

6.13.3 Epoxide Ring-Opening.

6.14 Addition and Elimination Reactions.

6.14.1 Michael Additions.

6.14.2 Addition to Alkenes.

6.14.3 Addition to Alkenes.

6.14.4 Addition to Nitriles.

6.15 Substitution Reactions.

6.16 Enamine and Imine Formations.

6.17 Reductive Aminations.

6.18 Ester and Amide Formation.

6.19 Decarboxylation Reactions.

6.20 Free Radical Reactions.

6.21 Protection/Deprotection Chemistry.

6.22 Preparation of Isotopically Labeled Compounds.

6.23 Miscellaneous Transformations.

6.24 Heterocycle Synthesis.

6.24.1 Three-Membered Heterocycles with One Heteroaton.

6.24.2 Four-Membered Heterocycles with One Heteroatom.

6.24.3 Five-Membered Heterocycles with One Heteroatom.

6.24.4 Five-Membered Heterocycles with Two Heteroatom.

6.24.5 Five-Membered Heterocycles with Three Heteroatom.

6.24.6 Five-Membered Heterocycles with Four Heteroatom.

6.24.7 Six-Membered Heterocycles with One Heteroatom.

6.24.8 Six-Membered Heterocycles with Two Heteroatom.

6.24.9 Six-Membered Heterocycles with Three Heteroatom.

6.24.10 Larger Heterocyclic and Polycyclic Ring Systems.

7. Literature Survey Part B: Combinatorial Chemistry and High-Throughput Organic Synthesis.

7.1 Solid-Phase Organic Synthesis.

7.1.1 Combinatorial Chemistry and Solid-Phase Organic Synthesis.

7.1.2 Microwave Chemistry and Solid-Phase Organic Synthesis.

7.1.3 Peptide Synthesis and Related Examples.

7.1.4 Resin Functionalization.

7.1.5 Transition Metal Catalysis.

7.1.6 Substitution Reactions.

7.1.7 Multicomponent Chemistry.

7.1.8 Microwave-Assisted Condensation Reactions.

7.1.9 Rearrangements.

7.1.10 Cleavage Reactions.

7.1.11 Miscellaneous.

7.2 Soluble Polymer-Supported Synthesis.

7.3 Fluorous Phase Organic Synthesis.

7.4 Grafted Ionic Liquid-Phase-Supported Synthesis.

7.5 Polymer-Supported Reagents.

7.6 Polymer-Supported Catalysts.

7.6.1 Catalysts on Polymeric Supports.

7.6.2 Silica-Grafted Catalysts.

7.6.3 Catalysts Immobilized on Glass.

7.6.4 Catalysts Immobilized on Carbon.

7.6.5 Miscellaneous.

7.7 Polymer-Supported Scavengers.

8. Outlook and Conclusions.

Index.

Product Details

ISBN:
9783527312108
Subtitle:
Microwaves in Organic and Medicinal Chemistry
Publisher:
Wiley-VCH
Author:
Stadler, Alexander
Author:
Folkers, Gerd
Author:
Mannhold, Raimund
Author:
Kubinyi, Hugo
Author:
Kappe, C. Oliver
Subject:
Chemistry - Organic
Subject:
Organic chemistry
Copyright:
Edition Description:
WOL online Book (not BRO)
Series:
Methods and Principles in Medicinal Chemistry
Series Volume:
14
Publication Date:
November 2005
Binding:
Online electronic file accessible through online networks
Grade Level:
Professional and scholarly
Language:
English
Pages:
422
Dimensions:
245 x 174.5 x 25.6 mm 33 oz

Related Subjects

Microwaves in Organic and Medicinal Chemistry
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Product details 422 pages Wiley-VCH - English 9783527312108 Reviews:
"Synopsis" by , The authors of this guide are experts on the use of microwaves for drug synthesis as well as having much experience in teaching courses held under the auspices of the American Chemical Society and the IUPAC.

In this handy source of information for any practicing synthetic chemist they focus on common reaction types in medicinal chemistry, including solid-phase and combinatorial methods. They consider the underlying theory, latest developments in microwave applications and include a variety of examples from recent literature, as well as less common applications that are equally relevant for organic and medicinal chemists.

An indispensable reference for researchers with an affinity to modern methods.

"Synopsis" by , A handy guide for organic and medicinal chemists focusing on common reaction types in medicinal chemistry, including solid-phase and combinatorial methods. Microwave theory, latest developments in instrumentation and a variety of examples from the recent literature are included.
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