Publication | Closed Access
[4 + 2] Cycloaromatization of 4-Bis(methylthio)-3-buten-2-one with Active Methylene Ketones: A Simple and Facile Phenol Annulation
33
Citations
47
References
2002
Year
Phenolic FunctionalityNovel OrganocatalystsBioorganic ChemistryEngineeringHeterocyclicNatural SciencesDiverse FrameworksOrganic ChemistryActive Methylene KetonesOrganometallic CatalysisSynthetic ChemistryChemistryFacile Phenol AnnulationHeterocycle ChemistryPharmacologyBeta-phenol AnnulationEnantioselective SynthesisBiomolecular Engineering
A new method for beta-phenol annulation involving base-induced [4C + 2C] cycloaromatization of readily available 4-bis(methylthio)-3-buten-2-one with a variety of cyclic and acyclic active methylene ketones has been reported. Appropriate choice of ketones allows synthesis of diverse frameworks such as dihydroindan, tetrahydronaphthalenes, their higher homologues, dihydro/octahydrophenanthrenes, anthracene, and heteroannulated analogue in high yields with regiocontrol of phenolic functionality.
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