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Privileged Structures in Drug Discovery : Medicinal Chemistry and Synthesis.

By: Material type: TextTextPublisher: Newark : John Wiley & Sons, Incorporated, 2018Copyright date: ©2018Edition: 1st edDescription: 1 online resource (561 pages)Content type:
  • text
Media type:
  • computer
Carrier type:
  • online resource
ISBN:
  • 9781118686331
Subject(s): Genre/Form: Additional physical formats: Print version:: Privileged Structures in Drug DiscoveryDDC classification:
  • 615.1/9
LOC classification:
  • RS403 .Y48 2018
Online resources:
Contents:
Intro -- Title Page -- Copyright Page -- Contents -- Chapter 1 Introduction -- 1.1 The Original Definition of Privileged Structures -- 1.2 The Role of Privileged Structures in the Drug Discovery Process -- 1.3 The Loose Definitions of "Privileged Structures" -- 1.4 Synthesis and Biological Activities of Carbocyclic and Heterocyclic Privileged Structures -- 1.4.1 Synthesis and Biological Activities of Three- and Four-Membered Ring Privileged Structures -- 1.4.2 Synthesis and Biological Activities of Five-Membered Ring Privileged Structures -- 1.4.3 Synthesis and Biological Activities of Six-Membered Ring Privileged Structures -- 1.4.4 Synthesis and Biological Activities of Bicyclic 5/5 and 6/5 Ring Privileged Structures -- 1.4.5 Synthesis and Biological Activities of Bicyclic 6/6 and 6/7 Ring Privileged Structures -- 1.4.6 Synthesis and Biological Activities of Tricyclic and Tetracyclic Ring Privileged Structures -- 1.5 Combinatorial Libraries of "Privileged Structures" -- 1.6 Scope of this Monograph -- References -- Chapter 2 Benzodiazepines -- 2.1 Introduction -- 2.2 Marketed BDZ Drugs -- 2.2.1 1,4-Benzodiazepine Marketed Drugs -- 2.2.2 1,5-Benzodiazepine Marketed Drugs -- 2.2.3 Linearly Fused BDZ Marketed Drugs -- 2.2.4 Angularly Fused-1,4-Benzodiazepine Marketed Drugs -- 2.3 Medicinal Chemistry Case Studies -- 2.3.1 Cardiovascular Applications -- 2.3.2 Central Nervous System Applications -- 2.3.3 Gastrointestinal Applications -- 2.3.4 Infectious Diseases Applications -- 2.3.5 Inflammation Applications -- 2.3.6 Metabolic Diseases Applications -- 2.3.7 Oncology Applications -- 2.4 Synthesis of BDZs -- 2.4.1 Condensation of o-Phenylenediamines to 1,5-Benzodiazepines -- 2.4.1.1 Condensation of o-Phenylenediamines with Ketones -- 2.4.1.2 Condensation of o-Phenylenediamines with α,β-Unsaturated Ketones.
2.4.1.3 Condensation of o-Phenylenediamines with Alkynes -- 2.4.2 Reductive Condensation of α-Substituted Nitrobenzenes with Ketones and α,β-Unsaturated Ketones -- 2.4.3 Intramolecular Cyclizations to 1,4-Benzodiazepines -- 2.4.3.1 Intramolecular Cyclizations-Path A -- 2.4.3.2 Intramolecular Cyclizations-Path B -- 2.4.3.3 Intramolecular Cyclizations-Path C -- 2.4.3.4 Intramolecular Cyclizations-Path D -- 2.4.3.5 Intramolecular Cyclizations-Path E -- 2.4.3.6 Intramolecular Cyclizations-Path F -- 2.4.3.7 Intramolecular Cyclizations-Path G -- 2.4.3.8 Intramolecular Cyclizations-Path H -- 2.4.4 Ugi Multicomponent Synthesis -- 2.4.5 Elaboration of 1,4-Benzodiazepines -- 2.4.6 Pyrrolo[2,1-c]benzodiazepines -- 2.4.7 Fused BDZ Ring Systems -- 2.4.8 Solid-Phase Synthesis of BDZs -- References -- Chapter 3 1,4-Dihydropyridines -- 3.1 Introduction -- 3.2 Marketed 1,4-Dihyropyridine Drugs -- 3.3 Medicinal Chemistry Case Studies -- 3.3.1 Cardiovascular Applications -- 3.3.2 Central Nervous System Applications -- 3.3.3 Infectious Diseases Applications -- 3.3.4 Inflammation Applications -- 3.3.5 Men's and Women's Health Issues Applications -- 3.3.6 Metabolic Diseases Applications -- 3.3.7 Oncology Applications -- 3.4 Synthesis of 1,4-Dihydropyridines -- 3.4.1 Classical Hantzsch Synthesis -- 3.4.2 Modified Hantzsch Conditions -- 3.4.3 1,4-Disubstituted-1,4-Dihydropyridines -- 3.4.4 Organometallic Additions to Pyridinium Salts -- 3.4.5 From Imines and Enamino Compounds -- 3.4.6 Multicomponent Synthesis -- 3.4.6.1 Three-Component Synthesis of 1,4-Dihydropyridines -- 3.4.6.2 Four-Component Synthesis of 1,4-Dihydropyridines -- 3.4.7 Organocatalytic Synthesis of 1,4-Dihydropyridines -- 3.4.8 Miscellaneous Preparations -- 3.4.9 Elaboration of 1,4-Dihydropyridines -- References -- Chapter 4 Biaryls -- 4.1 Introduction -- 4.2 Marketed Biaryl Drugs.
4.3 Medicinal Chemistry Case Studies -- 4.3.1 Cardiovascular Applications -- 4.3.2 Central Nervous System Applications -- 4.3.3 Infectious Diseases Applications -- 4.3.4 Inflammation Applications -- 4.3.5 Men's and Women's Health Issues Applications -- 4.3.6 Metabolic Diseases Applications -- 4.3.7 Oncology Applications -- 4.4 Synthesis of Biaryls -- 4.4.1 Transition Metal-Catalyzed Cross-Coupling Synthesis -- 4.4.1.1 Suzuki-Miyaura Cross-Coupling Reactions with Boronic Acids -- 4.4.1.2 Suzuki-Miyaura Cross-Coupling Reactions with Boronate Esters -- 4.4.1.3 Metal-Catalyzed Homocoupling Reactions -- 4.4.1.4 Uhlmann Coupling Reactions -- 4.4.1.5 Kumada-Tamao-Corriu Cross-Coupling Reactions -- 4.4.1.6 Negishi Cross-Coupling Reactions -- 4.4.1.7 Hiyama Cross-Coupling Reactions -- 4.4.1.8 Stille Cross-Coupling Reactions -- 4.4.1.9 Miscellaneous Cross-Coupling Reactions -- 4.4.1.10 Metal-Catalyzed Functional Group Removal Cross-Coupling Reaction -- 4.4.2 C─H Functionalization Reactions -- 4.4.2.1 Oxidative Coupling Reactions -- 4.4.2.2 Direct C─H Arylations -- 4.4.2.3 C─H Functionalization with Directing Groups -- 4.4.3 Cycloaddition Reactions -- 4.4.3.1 [3+3] Cycloaddition Reactions -- 4.4.3.2 [4+2] Cycloaddition Reactions -- 4.4.3.3 [2+2+2] Cycloaddition Reactions -- 4.4.3.4 Tandem Cycloaddition Reactions -- 4.4.4 Biaryl Phenol Syntheses -- 4.4.5 Miscellaneous Syntheses -- References -- Chapter 5 4-(Hetero)Arylpiperidines -- 5.1 Introduction -- 5.2 Marketed 4-(Hetero)Arylpiperidine Drugs -- 5.3 Medicinal Chemistry Case Studies -- 5.3.1 Cardiovascular Applications -- 5.3.2 Central Nervous System Applications -- 5.3.3 Infectious Diseases Applications -- 5.3.4 Inflammation Applications -- 5.3.5 Men's and Women's Health Applications -- 5.3.6 Metabolic Diseases Applications -- 5.3.7 Oncology Applications -- 5.4 Synthesis of 4-(Hetero)Arylpiperidines.
5.4.1 Preparation from 4-Piperidinones -- 5.4.2 Preparation from 4-Prefunctionalized- 3-alkenylpiperidines -- 5.4.3 Preparation from Negishi Cross-Coupling of 3-Zincated Piperidines -- 5.4.4 Preparation from 4-Funtionalized Piperidines -- 5.4.5 Conjugated Addition to Unsaturated Piperidines -- 5.4.6 Miscellaneous Syntheses -- References -- Chapter 6 Spiropiperidines -- 6.1 Introduction -- 6.2 Marketed Spiropiperidine Drugs -- 6.3 Medicinal Chemistry Case Studies -- 6.3.1 Cardiovascular Applications -- 6.3.2 Central Nervous System Applications -- 6.3.3 Infectious Diseases Applications -- 6.3.4 Inflammation Applications -- 6.3.5 Men's and Women's Health Applications -- 6.3.6 Metabolic Diseases Applications -- 6.3.7 Oncology Applications -- 6.4 Synthesis of Spiropiperidines -- 6.4.1 Quinolinylspiropiperidines -- 6.4.2 Azaspiro[5.5]alkane Systems -- 6.4.3 Diazaspiro[5.5]alkane Derivatives -- 6.4.4 1,4-Benzodioxinylspiropiperidines -- 6.4.5 Spirobenzooxazinylspiropiperidines -- 6.4.6 (Iso)Quinolinylspiropiperidines -- 6.4.7 Indenospiropiperidines -- 6.4.8 Indolin(on)ylspiropiperidines -- 6.4.9 Cyclohexadienonylspiropiperidines -- 6.4.10 Cyclopenta[b]pyrrolospiropiperidines -- 6.4.11 Chromanylspiropiperidines -- 6.4.12 (Iso)Benzofuran(on)ylspiropiperidines -- 6.4.13 Indenospiropiperidines -- References -- Chapter 7 2-Aminopyrimidines -- 7.1 Introduction -- 7.2 Marketed 2-Aminopyrimidine Drugs -- 7.3 Medicinal Chemistry Case Studies -- 7.3.1 Cardiovascular Applications -- 7.3.2 Central Nervous System Applications -- 7.3.3 Infectious Diseases Applications -- 7.3.4 Inflammation Applications -- 7.3.5 Metabolic Diseases Applications -- 7.3.6 Miscellaneous Applications -- 7.3.7 Oncology Applications -- 7.4 Synthesis of 2-Aminopyrimidines -- 7.4.1 Aminations with 2-Halo or 2,4-Dihalopyrimidines -- 7.4.2 Cross-Coupling Reactions with 2-Aminopyrimidines.
7.4.3 Aminations with 2-Sulfonylpyrimidines -- 7.4.4 Cyclizations with Guanidines -- References -- Chapter 8 2-Aminothiazoles -- 8.1 Introduction -- 8.2 Marketed 2-Aminothiazole Drugs -- 8.3 Medicinal Chemistry Case Studies -- 8.3.1 Cardiovascular Diseases Applications -- 8.3.2 Central Nervous System Applications -- 8.3.3 Infectious Diseases Applications -- 8.3.4 Inflammation Applications -- 8.3.5 Metabolic Diseases Applications -- 8.3.6 Oncology Applications -- 8.3.7 Miscellaneous Applications -- 8.4 Synthesis of 2-Aminothiazoles -- 8.4.1 Hantzsch Synthesis from α-Functionalized Ketones and Thioureas -- 8.4.2 Hantzsch Synthesis from Ketones and Thioureas -- 8.4.3 Synthesis from α-Haloketones and Thiocyanates -- 8.4.4 Synthesis from Vinyl Azides and Thiocyanates -- 8.4.5 Synthesis from Amidines and Thiocyanates -- 8.4.6 Synthesis from Alkenyl and Alkynyl Compounds with Thiocyanates or Thioureas -- 8.4.7 Miscellaneous Syntheses -- 8.4.8 Elaboration of 2-Aminothiazoles -- References -- Chapter 9 2-(Hetero)Arylindoles -- 9.1 Introduction -- 9.2 Marketed 2-Arylindole Drugs -- 9.3 Medicinal Chemistry Case Studies -- 9.3.1 Cardiovascular Applications -- 9.3.2 Central Nervous System Applications -- 9.3.3 Infectious Diseases Applications -- 9.3.4 Inflammation Applications -- 9.3.5 Men's and Women's Health Applications -- 9.3.6 Metabolic Diseases Applications -- 9.3.7 Miscellaneous Applications -- 9.3.8 Oncology Applications -- 9.4 Synthesis of 2‐(Hetero)Arylindoles -- 9.4.1 Functionalization to the Preformed Indole System -- 9.4.1.1 2-Functionalized Metallated Indoles with Aryl Halides (Strategy 1) -- 9.4.1.2 2-Halogenated or 2-Triflated Indoles with Functionalized Arenes (Strategy 1) -- 9.4.1.3 Direct Arylation of Indole with Functionalized Arenes (Strategy 2) -- 9.4.1.4 Direct Oxidative Coupling of Indoles with (Hetero)Arenes (Strategy 3).
9.4.2 Fischer Indole Synthesis.
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Intro -- Title Page -- Copyright Page -- Contents -- Chapter 1 Introduction -- 1.1 The Original Definition of Privileged Structures -- 1.2 The Role of Privileged Structures in the Drug Discovery Process -- 1.3 The Loose Definitions of "Privileged Structures" -- 1.4 Synthesis and Biological Activities of Carbocyclic and Heterocyclic Privileged Structures -- 1.4.1 Synthesis and Biological Activities of Three- and Four-Membered Ring Privileged Structures -- 1.4.2 Synthesis and Biological Activities of Five-Membered Ring Privileged Structures -- 1.4.3 Synthesis and Biological Activities of Six-Membered Ring Privileged Structures -- 1.4.4 Synthesis and Biological Activities of Bicyclic 5/5 and 6/5 Ring Privileged Structures -- 1.4.5 Synthesis and Biological Activities of Bicyclic 6/6 and 6/7 Ring Privileged Structures -- 1.4.6 Synthesis and Biological Activities of Tricyclic and Tetracyclic Ring Privileged Structures -- 1.5 Combinatorial Libraries of "Privileged Structures" -- 1.6 Scope of this Monograph -- References -- Chapter 2 Benzodiazepines -- 2.1 Introduction -- 2.2 Marketed BDZ Drugs -- 2.2.1 1,4-Benzodiazepine Marketed Drugs -- 2.2.2 1,5-Benzodiazepine Marketed Drugs -- 2.2.3 Linearly Fused BDZ Marketed Drugs -- 2.2.4 Angularly Fused-1,4-Benzodiazepine Marketed Drugs -- 2.3 Medicinal Chemistry Case Studies -- 2.3.1 Cardiovascular Applications -- 2.3.2 Central Nervous System Applications -- 2.3.3 Gastrointestinal Applications -- 2.3.4 Infectious Diseases Applications -- 2.3.5 Inflammation Applications -- 2.3.6 Metabolic Diseases Applications -- 2.3.7 Oncology Applications -- 2.4 Synthesis of BDZs -- 2.4.1 Condensation of o-Phenylenediamines to 1,5-Benzodiazepines -- 2.4.1.1 Condensation of o-Phenylenediamines with Ketones -- 2.4.1.2 Condensation of o-Phenylenediamines with α,β-Unsaturated Ketones.

2.4.1.3 Condensation of o-Phenylenediamines with Alkynes -- 2.4.2 Reductive Condensation of α-Substituted Nitrobenzenes with Ketones and α,β-Unsaturated Ketones -- 2.4.3 Intramolecular Cyclizations to 1,4-Benzodiazepines -- 2.4.3.1 Intramolecular Cyclizations-Path A -- 2.4.3.2 Intramolecular Cyclizations-Path B -- 2.4.3.3 Intramolecular Cyclizations-Path C -- 2.4.3.4 Intramolecular Cyclizations-Path D -- 2.4.3.5 Intramolecular Cyclizations-Path E -- 2.4.3.6 Intramolecular Cyclizations-Path F -- 2.4.3.7 Intramolecular Cyclizations-Path G -- 2.4.3.8 Intramolecular Cyclizations-Path H -- 2.4.4 Ugi Multicomponent Synthesis -- 2.4.5 Elaboration of 1,4-Benzodiazepines -- 2.4.6 Pyrrolo[2,1-c]benzodiazepines -- 2.4.7 Fused BDZ Ring Systems -- 2.4.8 Solid-Phase Synthesis of BDZs -- References -- Chapter 3 1,4-Dihydropyridines -- 3.1 Introduction -- 3.2 Marketed 1,4-Dihyropyridine Drugs -- 3.3 Medicinal Chemistry Case Studies -- 3.3.1 Cardiovascular Applications -- 3.3.2 Central Nervous System Applications -- 3.3.3 Infectious Diseases Applications -- 3.3.4 Inflammation Applications -- 3.3.5 Men's and Women's Health Issues Applications -- 3.3.6 Metabolic Diseases Applications -- 3.3.7 Oncology Applications -- 3.4 Synthesis of 1,4-Dihydropyridines -- 3.4.1 Classical Hantzsch Synthesis -- 3.4.2 Modified Hantzsch Conditions -- 3.4.3 1,4-Disubstituted-1,4-Dihydropyridines -- 3.4.4 Organometallic Additions to Pyridinium Salts -- 3.4.5 From Imines and Enamino Compounds -- 3.4.6 Multicomponent Synthesis -- 3.4.6.1 Three-Component Synthesis of 1,4-Dihydropyridines -- 3.4.6.2 Four-Component Synthesis of 1,4-Dihydropyridines -- 3.4.7 Organocatalytic Synthesis of 1,4-Dihydropyridines -- 3.4.8 Miscellaneous Preparations -- 3.4.9 Elaboration of 1,4-Dihydropyridines -- References -- Chapter 4 Biaryls -- 4.1 Introduction -- 4.2 Marketed Biaryl Drugs.

4.3 Medicinal Chemistry Case Studies -- 4.3.1 Cardiovascular Applications -- 4.3.2 Central Nervous System Applications -- 4.3.3 Infectious Diseases Applications -- 4.3.4 Inflammation Applications -- 4.3.5 Men's and Women's Health Issues Applications -- 4.3.6 Metabolic Diseases Applications -- 4.3.7 Oncology Applications -- 4.4 Synthesis of Biaryls -- 4.4.1 Transition Metal-Catalyzed Cross-Coupling Synthesis -- 4.4.1.1 Suzuki-Miyaura Cross-Coupling Reactions with Boronic Acids -- 4.4.1.2 Suzuki-Miyaura Cross-Coupling Reactions with Boronate Esters -- 4.4.1.3 Metal-Catalyzed Homocoupling Reactions -- 4.4.1.4 Uhlmann Coupling Reactions -- 4.4.1.5 Kumada-Tamao-Corriu Cross-Coupling Reactions -- 4.4.1.6 Negishi Cross-Coupling Reactions -- 4.4.1.7 Hiyama Cross-Coupling Reactions -- 4.4.1.8 Stille Cross-Coupling Reactions -- 4.4.1.9 Miscellaneous Cross-Coupling Reactions -- 4.4.1.10 Metal-Catalyzed Functional Group Removal Cross-Coupling Reaction -- 4.4.2 C─H Functionalization Reactions -- 4.4.2.1 Oxidative Coupling Reactions -- 4.4.2.2 Direct C─H Arylations -- 4.4.2.3 C─H Functionalization with Directing Groups -- 4.4.3 Cycloaddition Reactions -- 4.4.3.1 [3+3] Cycloaddition Reactions -- 4.4.3.2 [4+2] Cycloaddition Reactions -- 4.4.3.3 [2+2+2] Cycloaddition Reactions -- 4.4.3.4 Tandem Cycloaddition Reactions -- 4.4.4 Biaryl Phenol Syntheses -- 4.4.5 Miscellaneous Syntheses -- References -- Chapter 5 4-(Hetero)Arylpiperidines -- 5.1 Introduction -- 5.2 Marketed 4-(Hetero)Arylpiperidine Drugs -- 5.3 Medicinal Chemistry Case Studies -- 5.3.1 Cardiovascular Applications -- 5.3.2 Central Nervous System Applications -- 5.3.3 Infectious Diseases Applications -- 5.3.4 Inflammation Applications -- 5.3.5 Men's and Women's Health Applications -- 5.3.6 Metabolic Diseases Applications -- 5.3.7 Oncology Applications -- 5.4 Synthesis of 4-(Hetero)Arylpiperidines.

5.4.1 Preparation from 4-Piperidinones -- 5.4.2 Preparation from 4-Prefunctionalized- 3-alkenylpiperidines -- 5.4.3 Preparation from Negishi Cross-Coupling of 3-Zincated Piperidines -- 5.4.4 Preparation from 4-Funtionalized Piperidines -- 5.4.5 Conjugated Addition to Unsaturated Piperidines -- 5.4.6 Miscellaneous Syntheses -- References -- Chapter 6 Spiropiperidines -- 6.1 Introduction -- 6.2 Marketed Spiropiperidine Drugs -- 6.3 Medicinal Chemistry Case Studies -- 6.3.1 Cardiovascular Applications -- 6.3.2 Central Nervous System Applications -- 6.3.3 Infectious Diseases Applications -- 6.3.4 Inflammation Applications -- 6.3.5 Men's and Women's Health Applications -- 6.3.6 Metabolic Diseases Applications -- 6.3.7 Oncology Applications -- 6.4 Synthesis of Spiropiperidines -- 6.4.1 Quinolinylspiropiperidines -- 6.4.2 Azaspiro[5.5]alkane Systems -- 6.4.3 Diazaspiro[5.5]alkane Derivatives -- 6.4.4 1,4-Benzodioxinylspiropiperidines -- 6.4.5 Spirobenzooxazinylspiropiperidines -- 6.4.6 (Iso)Quinolinylspiropiperidines -- 6.4.7 Indenospiropiperidines -- 6.4.8 Indolin(on)ylspiropiperidines -- 6.4.9 Cyclohexadienonylspiropiperidines -- 6.4.10 Cyclopenta[b]pyrrolospiropiperidines -- 6.4.11 Chromanylspiropiperidines -- 6.4.12 (Iso)Benzofuran(on)ylspiropiperidines -- 6.4.13 Indenospiropiperidines -- References -- Chapter 7 2-Aminopyrimidines -- 7.1 Introduction -- 7.2 Marketed 2-Aminopyrimidine Drugs -- 7.3 Medicinal Chemistry Case Studies -- 7.3.1 Cardiovascular Applications -- 7.3.2 Central Nervous System Applications -- 7.3.3 Infectious Diseases Applications -- 7.3.4 Inflammation Applications -- 7.3.5 Metabolic Diseases Applications -- 7.3.6 Miscellaneous Applications -- 7.3.7 Oncology Applications -- 7.4 Synthesis of 2-Aminopyrimidines -- 7.4.1 Aminations with 2-Halo or 2,4-Dihalopyrimidines -- 7.4.2 Cross-Coupling Reactions with 2-Aminopyrimidines.

7.4.3 Aminations with 2-Sulfonylpyrimidines -- 7.4.4 Cyclizations with Guanidines -- References -- Chapter 8 2-Aminothiazoles -- 8.1 Introduction -- 8.2 Marketed 2-Aminothiazole Drugs -- 8.3 Medicinal Chemistry Case Studies -- 8.3.1 Cardiovascular Diseases Applications -- 8.3.2 Central Nervous System Applications -- 8.3.3 Infectious Diseases Applications -- 8.3.4 Inflammation Applications -- 8.3.5 Metabolic Diseases Applications -- 8.3.6 Oncology Applications -- 8.3.7 Miscellaneous Applications -- 8.4 Synthesis of 2-Aminothiazoles -- 8.4.1 Hantzsch Synthesis from α-Functionalized Ketones and Thioureas -- 8.4.2 Hantzsch Synthesis from Ketones and Thioureas -- 8.4.3 Synthesis from α-Haloketones and Thiocyanates -- 8.4.4 Synthesis from Vinyl Azides and Thiocyanates -- 8.4.5 Synthesis from Amidines and Thiocyanates -- 8.4.6 Synthesis from Alkenyl and Alkynyl Compounds with Thiocyanates or Thioureas -- 8.4.7 Miscellaneous Syntheses -- 8.4.8 Elaboration of 2-Aminothiazoles -- References -- Chapter 9 2-(Hetero)Arylindoles -- 9.1 Introduction -- 9.2 Marketed 2-Arylindole Drugs -- 9.3 Medicinal Chemistry Case Studies -- 9.3.1 Cardiovascular Applications -- 9.3.2 Central Nervous System Applications -- 9.3.3 Infectious Diseases Applications -- 9.3.4 Inflammation Applications -- 9.3.5 Men's and Women's Health Applications -- 9.3.6 Metabolic Diseases Applications -- 9.3.7 Miscellaneous Applications -- 9.3.8 Oncology Applications -- 9.4 Synthesis of 2‐(Hetero)Arylindoles -- 9.4.1 Functionalization to the Preformed Indole System -- 9.4.1.1 2-Functionalized Metallated Indoles with Aryl Halides (Strategy 1) -- 9.4.1.2 2-Halogenated or 2-Triflated Indoles with Functionalized Arenes (Strategy 1) -- 9.4.1.3 Direct Arylation of Indole with Functionalized Arenes (Strategy 2) -- 9.4.1.4 Direct Oxidative Coupling of Indoles with (Hetero)Arenes (Strategy 3).

9.4.2 Fischer Indole Synthesis.

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