Angewandte Chemie International Edition · 2009 · 104 citations · 16 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisOrganic SynthesisCatalytic IsomerizationHeterocycle FunctionalizationIndazole SynthesisIsomerization CatalysisMild Reaction ConditionsRegioselective Catalysis
Practical and highly versatile, the reaction of readily available (2-chlorophenyl)acetylene and hydrazine substrates affords substituted 2H-indazoles in just a few hours under very mild reaction conditions (see scheme; DMF=N,N-dimethylformamide). The catalyzed domino sequence consists of a regioselective coupling followed by an intramolecular hydroamination and subsequent isomerization of the resulting exocyclic bond.
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J. I. G. Cadogan, M. Cameron-Wood, Raymond K. Mackie et al. · Journal of the Chemical Society (Resumed) · 1965 · 314 citations