Chemistry Letters · 1979 · 16 citations · 5 references
Natural SciencesChemistryMedicinal ChemistryOrganic ChemistryOrganometallic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsOrganic SynthesisIndole ChemistryIndole Synthesis
Abstract Indolyllithium arising from ring-closure of o-lithiomethylphenyl isocyanide, which is generated in situ by the reaction of o-tolyl isocyanide with lithium diisopropylamide in diglyme at −78°C, is treated with anhydrous MgI2 prior to alkylations with alkyl halides to give 3-alkylindoles selectively in moderate to excellent yields. The reaction provides a convenient method for synthesis of 3-alkylindoles starting with o-tolyl isocyanide.
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