Multicomponent reactions towards heterocycles : concepts and applications / edited by Erik Van der Eycken, Upendra K. Sharma.

Format:

Book

Contributor:

Eycken, Erik van der, editor.

Sharma, Upendra K., editor.

Alumni and Friends Memorial Book Fund.

Language:

English

Subjects (All):

Heterocyclic compounds--Synthesis.

Heterocyclic compounds.

Chemical reactions.

Physical Description:

xii, 604 pages : illustrations (some color) ; 25 cm

Place of Publication:

Weinheim, Germany : Wiley-VCH, [2022]

Contents:

Machine generated contents note: 1.1. Introduction / Ouldouz Ghashghaei / Marina Pedrola / Carmen Escolano / Rodolfo Lavilla

1.2. Concerted MCRs / Ouldouz Ghashghaei / Marina Pedrola / Carmen Escolano / Rodolfo Lavilla

1.3. Radical MCRs / Ouldouz Ghashghaei / Marina Pedrola / Carmen Escolano / Rodolfo Lavilla

1.4. Metal-catalyzed MCRs / Ouldouz Ghashghaei / Marina Pedrola / Carmen Escolano / Rodolfo Lavilla

1.5. Carbonyl/Imine Polar MCRs / Ouldouz Ghashghaei / Marina Pedrola / Carmen Escolano / Rodolfo Lavilla

1.6. Isocyanide-based MCRs / Ouldouz Ghashghaei / Marina Pedrola / Carmen Escolano / Rodolfo Lavilla

1.7. Miscellany Processes / Ouldouz Ghashghaei / Marina Pedrola / Carmen Escolano / Rodolfo Lavilla

1.8. Conclusion / Ouldouz Ghashghaei / Marina Pedrola / Carmen Escolano / Rodolfo Lavilla

Acknowledgment / Ouldouz Ghashghaei / Marina Pedrola / Carmen Escolano / Rodolfo Lavilla

References / Ouldouz Ghashghaei / Marina Pedrola / Carmen Escolano / Rodolfo Lavilla

2.1. Introduction / Susan Sieben / Jordy M. Saya / Dean Johnson / Romano V.A. Orru

2.2. Ugi-type Multicomponent Polymerizations / Susan Sieben / Jordy M. Saya / Dean Johnson / Romano V.A. Orru

2.3. Mannich-type Multicomponent Polymerizations / Susan Sieben / Jordy M. Saya / Dean Johnson / Romano V.A. Orru

2.4. Biginelli-type Multicomponent Polymerizations / Susan Sieben / Jordy M. Saya / Dean Johnson / Romano V.A. Orru

2.5. Hantzsch-type Multicomponent Polymerizations / Susan Sieben / Jordy M. Saya / Dean Johnson / Romano V.A. Orru

2.6. Debus-Radziszewski-type Multicomponent Polymerizations / Susan Sieben / Jordy M. Saya / Dean Johnson / Romano V.A. Orru

2.7. Other Multicomponent Polymerizations / Susan Sieben / Jordy M. Saya / Dean Johnson / Romano V.A. Orru

2.7.1. The Cu(I)-catalyzed MCP of Diynes, Azides, and Carbodiimides/Nitriles / Susan Sieben / Jordy M. Saya / Dean Johnson / Romano V.A. Orru

2.7.2. The Pd-catalyzed MCP of Imines, Acyl Chlorides, and N-Sulfonyl Imines / Susan Sieben / Jordy M. Saya / Dean Johnson / Romano V.A. Orru

2.7.3. The Mercaptoacetic Acid Locking Imine Reaction / Susan Sieben / Jordy M. Saya / Dean Johnson / Romano V.A. Orru

2.8. Conclusions and Outlook / Susan Sieben / Jordy M. Saya / Dean Johnson / Romano V.A. Orru

References / Susan Sieben / Jordy M. Saya / Dean Johnson / Romano V.A. Orru

3.1. Introduction / Zefeng Wang / Alexander Domling

3.1.1. Example: Protein-Protein Interaction p53-MDM2 / Zefeng Wang / Alexander Domling

3.2. Scaffolds and the Chemical Space of MCR / Zefeng Wang / Alexander Domling

3.2.1. Marketed and Clinical Stage Drugs / Zefeng Wang / Alexander Domling

3.3. Some Biopharmaceutical Application of MCR / Zefeng Wang / Alexander Domling

3.3.1. Computational Methods of MCR Chemical Space Screening / Zefeng Wang / Alexander Domling

3.4. Conclusion / Zefeng Wang / Alexander Domling

References / Zefeng Wang / Alexander Domling

4.1. Introduction / Leonardo G. Ceballos / Daylin F. Pacheco / Bernhard Westermann / Daniel G. Rivera

4.2. Synthesis of Five-Membered Ring Heterocycles / Leonardo G. Ceballos / Daylin F. Pacheco / Bernhard Westermann / Daniel G. Rivera

4.3. Synthesis of Six-Membered Ring Heterocycles / Leonardo G. Ceballos / Daylin F. Pacheco / Bernhard Westermann / Daniel G. Rivera

4.4. Synthesis of Fused Heterocyclic Ring Systems / Leonardo G. Ceballos / Daylin F. Pacheco / Bernhard Westermann / Daniel G. Rivera

4.5. Synthesis of Heterocycles on Solid-Supported Amino Acids / Leonardo G. Ceballos / Daylin F. Pacheco / Bernhard Westermann / Daniel G. Rivera

4.6. Solid-Phase Multicomponent Construction of DNA-Encoded Heterocycle Libraries / Leonardo G. Ceballos / Daylin F. Pacheco / Bernhard Westermann / Daniel G. Rivera

4.7. Miscellaneous Supports for Multicomponent Synthesis of Heterocycles / Leonardo G. Ceballos / Daylin F. Pacheco / Bernhard Westermann / Daniel G. Rivera

4.8. Conclusions / Leonardo G. Ceballos / Daylin F. Pacheco / Bernhard Westermann / Daniel G. Rivera

References / Leonardo G. Ceballos / Daylin F. Pacheco / Bernhard Westermann / Daniel G. Rivera

5.1. Introduction / Wei Zhang

5.2. High-Order MCRs / Wei Zhang

5.3. Consecutive MCRs / Wei Zhang

5.4. MCRs Followed by Cyclization Reactions / Wei Zhang

5.5. MCRs Followed by Cycloaddition or Annulation Reactions / Wei Zhang

5.6. Conclusion and Outlook / Wei Zhang

References / Wei Zhang

6.1. Introduction / Chiara Lambruschini / Lisa Moni / Andrea Basso

6.2. Multicomponent Reactions Under Standard Flow Conditions / Chiara Lambruschini / Lisa Moni / Andrea Basso

6.3. Multicomponent Reactions with Hazardous Reagents / Chiara Lambruschini / Lisa Moni / Andrea Basso

6.4. Multicomponent Reactions Under Special Conditions / Chiara Lambruschini / Lisa Moni / Andrea Basso

6.4.1. Reactions with Microwave or Inductive Heating / Chiara Lambruschini / Lisa Moni / Andrea Basso

6.4.2. Reactions with Active Packed-Bed Columns / Chiara Lambruschini / Lisa Moni / Andrea Basso

6.4.3. Reactions Under Other Conditions / Chiara Lambruschini / Lisa Moni / Andrea Basso

6.5. Telescoped Reactions / Chiara Lambruschini / Lisa Moni / Andrea Basso

6.6. Conclusions / Chiara Lambruschini / Lisa Moni / Andrea Basso

References / Chiara Lambruschini / Lisa Moni / Andrea Basso

7.1. Introduction / Alexey A. Festa / Leonid G. Voskressensky

7.2. Transition-metal-involved C-H Functionalization / Alexey A. Festa / Leonid G. Voskressensky

7.2.1. Multicomponent Synthesis of Heterocycles Through C-H Functionalization / Alexey A. Festa / Leonid G. Voskressensky

7.3. Transition-metal-involved C-H Functionalization / Alexey A. Festa / Leonid G. Voskressensky

7.3.1. Multicomponent C-H Functionalization of Heterocycles / Alexey A. Festa / Leonid G. Voskressensky

7.3.1.1. C(sp2)-H Functionalization / Alexey A. Festa / Leonid G. Voskressensky

7.3.1.2. C(sp3)-H Functionalization / Alexey A. Festa / Leonid G. Voskressensky

7.4. Transition-metal-free C-H Functionalization / Alexey A. Festa / Leonid G. Voskressensky

7.4.1. Multicomponent Synthesis of Heterocycles Through C-H-functionalization / Alexey A. Festa / Leonid G. Voskressensky

7.4.2. Multicomponent C-H Functionalization of Heterocycles / Alexey A. Festa / Leonid G. Voskressensky

References / Alexey A. Festa / Leonid G. Voskressensky

References / Valentyn A. Chebanov / Serhiy M. Desenko / Victoria V. Lipson / Nikolay Yu.

Gorobets

9.1. Introduction / Nathan Bedard / Alessandra Fistrovich / Kevin Schofield / Arthur Shaw / Christopher Hulme

9.2. Multicomponent Reactions / Nathan Bedard / Alessandra Fistrovich / Kevin Schofield / Arthur Shaw / Christopher Hulme

9.3. The Ugi Reaction / Nathan Bedard / Alessandra Fistrovich / Kevin Schofield / Arthur Shaw / Christopher Hulme

9.3.1. The Ugi Reaction Used in Natural Product Synthesis / Nathan Bedard / Alessandra Fistrovich / Kevin Schofield / Arthur Shaw / Christopher Hulme

9.3.2. The Ugi Reaction in FDA-approved Drugs and Drug Candidates / Nathan Bedard / Alessandra Fistrovich / Kevin Schofield / Arthur Shaw / Christopher Hulme

9.3.2.1. Synthesis of Lipitor Using Ugi 4CR / Nathan Bedard / Alessandra Fistrovich / Kevin Schofield / Arthur Shaw / Christopher Hulme

9.3.2.2. Synthesis of Ivosidenib Utilizing Ugi 4CR / Nathan Bedard / Alessandra Fistrovich / Kevin Schofield / Arthur Shaw / Christopher Hulme

9.3.3. Rapid Lead Optimization with Ugi 4CR / Kevin Schofield / Arthur Shaw / Alessandra Fistrovich / Nathan Bedard / Christopher Hulme

9.4. The Passerini Reaction / Nathan Bedard / Alessandra Fistrovich / Kevin Schofield / Arthur Shaw / Christopher Hulme

9.4.1. The Passerini Reaction in Natural Products / Alessandra Fistrovich / Nathan Bedard / Kevin Schofield / Christopher Hulme / Arthur Shaw

9.5. Groebke-Blackburn-Bienayme (GBB-3CR) MCR / Nathan Bedard / Alessandra Fistrovich / Kevin Schofield / Arthur Shaw / Christopher Hulme

9.6. Gewald (G-3CR) Reaction / Nathan Bedard / Alessandra Fistrovich / Arthur Shaw / Kevin Schofield / Christopher Hulme

9.7. The Hantzsch Dihydropyridine (DHP) Synthesis / Arthur Shaw / Kevin Schofield / Alessandra Fistrovich / Nathan Bedard / Christopher Hulme

9.7.1. FDA-approved Hantzsch Dihydropyridines / Arthur Shaw / Kevin Schofield / Alessandra Fistrovich / Nathan Bedard / Christopher Hulme

9.7.2. Anti-bacterial Hantzsch DHPs / Nathan Bedard / Alessandra Fistrovich / Kevin Schofield / Arthur Shaw / Christopher Hulme

9.8. The Biginelli Reaction / Arthur Shaw / Kevin Schofield / Alessandra Fistrovich / Nathan Bedard / Christopher Hulme

9.8.1. Biginelli Reactions and Natural Products / Alessandra Fistrovich / Nathan Bedard / Kevin Schofield / Arthur Shaw / Christopher Hulme

9.8.2. Biginelli DHPMs as CNS Agents / Alessandra Fistrovich / Nathan Bedard / Kevin Schofield / Christopher Hulme / Arthur Shaw

9.8.3. Biginelli Products Antitumor Capabilities / Nathan Bedard / Alessandra Fistrovich / Arthur Shaw / Kevin Schofield / Christopher Hulme

9.9. van Leusen Reaction / Christopher Hulme / Nathan Bedard / Alessandra Fistrovich / Kevin Schofield / Arthur Shaw

9.9.1. Tosmic-mediated Cyclization Toward Nitrogen-containing Heterocycles / Nathan Bedard / Alessandra Fistrovich / Christopher Hulme / Arthur Shaw / Kevin Schofield

Contents note continued: 9.9.2. Applications of the van Leusen Reaction / Nathan Bedard / Alessandra Fistrovich / Christopher Hulme / Arthur Shaw / Kevin Schofield

9.9.2.1. Sequential One-pot Three-step 3C-van Leusen Reaction/Deprotection/Cyclization / Kevin Schofield / Christopher Hulme / Arthur Shaw / Alessandra Fistrovich / Nathan Bedard

9.9.2.2. Sequential van Leusen Reaction/Staudinger/aza-Wittig/Cyclization / Nathan Bedard / Alessandra Fistrovich / Christopher Hulme / Arthur Shaw / Kevin Schofield

9.9.2.3. DNA-conjugated van Leusen Reaction / Christopher Hulme / Alessandra Fistrovich / Nathan Bedard / Arthur Shaw / Kevin Schofield

9.9.3. Applications of the van Leusen Reaction in Drug Discovery / Arthur Shaw / Christopher Hulme / Kevin Schofield / Alessandra Fistrovich / Nathan Bedard

9.9.3.1. Purinergic P2X7 Receptor Antagonists / Arthur Shaw / Kevin Schofield / Christopher Hulme / Alessandra Fistrovich / Nathan Bedard

9.9.3.2. Indoleamine 2,3-Dioxygenase (IDO1) Inhibitors / Nathan Bedard / Arthur Shaw / Kevin Schofield / Alessandra Fistrovich / Christopher Hulme

9.9.3.3. Disruptors of P53/MDM2 Protein-Protein Interactions / Christopher Hulme / Arthur Shaw / Kevin Schofield / Alessandra Fistrovich / Nathan Bedard

9.9.3.4. Disruptors of PCSK9/LDLR Protein-Protein Interactions / Christopher Hulme / Kevin Schofield / Alessandra Fistrovich / Nathan Bedard / Arthur Shaw

9.9.3.5. Inhibitors of TGFβR1 as Immuno-oncology Therapeutics / Christopher Hulme / Alessandra Fistrovich / Kevin Schofield / Arthur Shaw / Nathan Bedard

References / Alessandra Fistrovich / Nathan Bedard / Arthur Shaw / Christopher Hulme / Kevin Schofield

10.1. Introduction / Thomas J.J. Muller / Jonas Niedballa

10.2. Catalytic Generation of Alkynones / Thomas J.J. Muller / Jonas Niedballa

10.3. Multicomponent Syntheses of Five-membered Heterocycles / Jonas Niedballa / Thomas J.J. Muller

10.3.1. Pyrazolines / Jonas Niedballa / Thomas J.J. Muller

10.3.2. Pyrazoles / Jonas Niedballa / Thomas J.J. Muller

10.3.3. Isoxazoles / Jonas Niedballa / Thomas J.J. Muller

10.3.4. Triazoles / Jonas Niedballa / Thomas J.J. Muller

10.3.5. Thiophenes / Jonas Niedballa / Thomas J.J. Muller

10.3.6. Indolones / Jonas Niedballa / Thomas J.J. Muller

10.4. Multicomponent Syntheses of Six-membered Heterocycles / Jonas Niedballa / Thomas J.J. Muller

10.4.1. Pyranones / Jonas Niedballa / Thomas J.J. Muller

10.4.2. Pyridines / Jonas Niedballa / Thomas J.J. Muller

10.4.3. Pyrimidines / Jonas Niedballa / Thomas J.J. Muller

10.4.4. Oxazaborinines / Jonas Niedballa / Thomas J.J. Muller

10.4.5. Coumarines / Jonas Niedballa / Thomas J.J. Muller

10.4.6. Quinolines / Jonas Niedballa / Thomas J.J. Muller

10.4.7. Quinoxalines / Jonas Niedballa / Thomas J.J. Muller

10.5. Conclusion and Outlook / Jonas Niedballa / Thomas J.J. Muller

References / Jonas Niedballa / Thomas J.J. Muller

11.1. Introduction / Carlos K.Z. Andrade / Carlos E.M. Salvador / Thaissa P.F. Rosalba / Lucilia Z.A. Correa / Luan A. Martinho / Yuri R.B. Sousa

11.2. Three-membered Ring Heterocycles / Carlos K.Z. Andrade / Carlos E.M. Salvador / Thaissa P.F. Rosalba / Lucilia Z.A. Correa / Luan A. Martinho / Yuri R.B. Sousa

11.3. Four-membered Ring Heterocycles / Carlos K.Z. Andrade / Carlos E.M. Salvador / Thaissa P.F. Rosalba / Lucilia Z.A. Correa / Luan A. Martinho / Yuri R.B. Sousa

11.4. Five-membered Ring Heterocycles / Carlos K.Z. Andrade / Carlos E.M. Salvador / Thaissa P.F. Rosalba / Lucilia Z.A. Correa / Luan A. Martinho / Yuri R.B. Sousa

11.5. Six-membered Ring Heterocycles / Carlos K.Z. Andrade / Carlos E.M. Salvador / Thaissa P.F. Rosalba / Lucilia Z.A. Correa / Luan A. Martinho / Yuri R.B. Sousa

11.6. Seven-membered Ring Heterocycles / Carlos K.Z. Andrade / Carlos E.M. Salvador / Thaissa P.F. Rosalba / Lucilia Z.A. Correa / Luan A. Martinho / Yuri R.B. Sousa

11.7. Macrocycles / Carlos K.Z. Andrade / Carlos E.M. Salvador / Thaissa P.F. Rosalba / Lucilia Z.A. Correa / Luan A. Martinho / Yuri R.B. Sousa

11.8. Fused Heterocycles / Carlos K.Z. Andrade / Carlos E.M. Salvador / Thaissa P.F. Rosalba / Lucilia Z.A. Correa / Luan A. Martinho / Yuri R.B. Sousa

11.9. Spiro Heterocycles / Carlos K.Z. Andrade / Carlos E.M. Salvador / Thaissa P.F. Rosalba / Lucilia Z.A. Correa / Luan A. Martinho / Yuri R.B. Sousa

References / Carlos K.Z. Andrade / Carlos E.M. Salvador / Thaissa P.F. Rosalba / Lucilia Z.A. Correa / Luan A. Martinho / Yuri R.B. Sousa

12.1. Introduction / Melody E. Boetius / Eelco Ruijter

12.2. Imine-based MCRs / Melody E. Boetius / Eelco Ruijter

12.2.1. Strecker Reaction / Melody E. Boetius / Eelco Ruijter

12.2.2. Mannich Reaction / Melody E. Boetius / Eelco Ruijter

12.2.2.1. Aza-Henry Reaction / Melody E. Boetius / Eelco Ruijter

12.2.2.2. Petasis Reaction / Melody E. Boetius / Eelco Ruijter

12.2.2.3. Aza-Diels-Alder Via Mannich Reaction Pathway / Melody E. Boetius / Eelco Ruijter

12.2.2.4. [2 + 2 + 2]-Cycloaddition / Melody E. Boetius / Eelco Ruijter

12.2.3. Hantzsch Reaction / Melody E. Boetius / Eelco Ruijter

12.2.4. Biginelli Reaction / Melody E. Boetius / Eelco Ruijter

12.3. Michael Addition-based MCRs / Melody E. Boetius / Eelco Ruijter

12.3.1. Oxa-Michael/Michael/Michael/Aldol Condensation Cascade Reactions / Melody E. Boetius / Eelco Ruijter

12.3.2. Knoevenagel-Michael Cascade Reaction / Melody E. Boetius / Eelco Ruijter

12.3.3. Michael-Henry Cascade Reaction / Melody E. Boetius / Eelco Ruijter

12.4. Isocyanide-Based MCRs / Melody E. Boetius / Eelco Ruijter

12.4.1. Passerini Reactions / Melody E. Boetius / Eelco Ruijter

12.4.1.1. Passerini-type Two-component Reactions / Melody E. Boetius / Eelco Ruijter

12.4.1.2. Passerini Three-component Reaction / Melody E. Boetius / Eelco Ruijter

12.4.2. Isocyanide-Based [3 + 2]-Cycloaddition / Melody E. Boetius / Eelco Ruijter

12.4.3. Ugi-type Reactions / Melody E. Boetius / Eelco Ruijter

12.5. Conclusion / Melody E. Boetius / Eelco Ruijter

References / Melody E. Boetius / Eelco Ruijter

13.1. Introduction / Lilia Fuentes-Morales / Luis D. Miranda

13.2. Five-membered Heterocycles with One Heteroatom / Lilia Fuentes-Morales / Luis D. Miranda

13.3. Five-membered Systems with Two Heteroatoms / Lilia Fuentes-Morales / Luis D. Miranda

13.4. Five-membered Systems with Three Heteroatoms / Lilia Fuentes-Morales / Luis D. Miranda

13.5. Six-membered Heterocycles with One Heteroatom and Their Benzo-fused Derivatives / Lilia Fuentes-Morales / Luis D. Miranda

13.6. Six-membered 0-heterocycles and their Benzofused Derivatives / Lilia Fuentes-Morales / Luis D. Miranda

13.7. Four-membered N-heterocycles and Seven-membered Benzofused N-heterocycles / Lilia Fuentes-Morales / Luis D. Miranda

13.8. Conclusion / Lilia Fuentes-Morales / Luis D. Miranda

References / Lilia Fuentes-Morales / Luis D. Miranda.

Notes:

Includes bibliographical references and index.

Local Notes:

Acquired for the Penn Libraries with assistance from the Alumni and Friends Memorial Book Fund.

Other Format:

Electronic version: Multicomponent reactions towards heterocycles.

ISBN:

9783527349081

3527349081

OCLC:

1285706270

Publisher Number:

99990869116