SYNTHESIS OF DERIVATIVES STRUCTURALLY RELATED TO GLAZIOVINE

Article abstract of DOI:10.1016/S0040-4020(01)82450-9

Three compounds, 2a, 2b, and 2c have been synthesized by an analogy with glaziovine 1 which has been claimed to have anxiolytic properties similar to diazepam.The intermediates indanones 5 have been obtained according to conventional (for 5a) or less conventional procedure (5b) and then converted to the corresponding indanones 11.Michael addition of methylbenzylamine followed by a one-carbon homologation of the ketone gave an aldehyde suitable for Robinson annulation leading to the spiro compounds 2.DDQ oxidation gave 3.No anxiolytic activity was found from the pharmacological data.