Indoles: Reaction and Synthesis

BENZOTHIOPHENES, BENZOFURANS, ISOINDOLES,

BENZOTHIOPHENES AND ISOBENZOFURANS
Typical Reactivity of Indoles
Benzo[ b ]thiophenes, Benzo[ b ]furans, Isoindoles,Benzo[ c ]thiophenes and Isobenzofurans
Indoles: Reactions
Reactions with Electrophilic Reagents-
Substitution at Carbon-Protonation
Nitration; Reactions with Other Nitrogen Electrophiles
Sulfonation; Reactions with Other Sulfur Electrophiles
Acylation
Alkylation
Reactions with Aldehydes and Ketones
Reactions with Iminium Ions: Mannich Reactions
Reactions with Oxidizing Agents
Oxidative cleavage
Oxindoles
Reactions with Nucleophilic Reagents
Reactions with Bases-
Deprotonation of N - Hydrogen and Reactions of Indolyl Anions
Reactions with Reducing Agents
Isatin
1 - Hydroxyindole
Amino - Indoles
Aza - Indoles
Synthesis of Indoles
Ring Synthesis of Indoles-
From Aryl - hydrazones of Aldehydes and Ketones

The Fischer Synthesis

From ortho - (2 - Oxoalkyl) - Anilines and Equivalents
The Reissert Synthesis
From ortho - Nitro - Styrenes
From ortho - Alkynyl - Arylamines
Sonogashira reactions
From ortho -Halo Aryl - Amines and Alkynes
From ortho - Toluidides
The Madelung Synthesis
From α - Arylamino - Carbonyl
Compounds
The Bischler Synthesis
From Pyrroles
From ortho - Substituted Nitro - Arenes
Bartoli Synthesis
From N - Aryl Enamines
From Enamines and p - Benzoquinones
The Nenitzescu Synthesis
From Aryl - Amines
The Gassman Synthesis
From ortho - Acyl - Anilides
The Fürstner Synthesis
By Cyclisation of Nitrenes
Ring Synthesis of Isatins
Example of Notable Indole Syntheses
Ondansetron-(Onset)