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RESEARCH PRODUCT
Two-Step Route to Indoles and Analogues from Haloarenes: A Variation on the Fischer Indole Synthesis
Martyn InmanChristopher J. MoodyAnna Carbonesubject
Indole testQuenching (fluorescence)IndolesHalogenationChemistryArylOrganic ChemistryTwo stepFischer synthesiHalogenationGreen Chemistry TechnologyChemistry Techniques SyntheticHydrocarbons AromaticSettore CHIM/08 - Chimica Farmaceuticachemistry.chemical_compoundIndoleFischer indole synthesisOrganic chemistrythienopyrrolesMagnesiumFischer synthesis; Indoles; azaindoles; thienopyrrolesFischer synthesisazaindolesazaindoledescription
In a new variation on the Fischer indole synthesis, readily available haloarenes are converted into a wide range of indoles in just two steps by halogen-magnesium exchange and quenching with di-tert-butyl azodicarboxylate, followed by reaction with aldehydes or ketones under acidic conditions. The protocol, which is readily extended to the preparation of indole isosteres, 4- and 6-azaindoles and thienopyrroles, obviates the need to prepare potentially toxic aryl hydrazines, simultaneously avoiding undesirable anilines such as naphthylamines.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2012-01-01 |