Recueil des Travaux Chimiques des Pays-Bas p. 145 - 152 (1994)
Update date:2022-08-03
Topics:
Rutjes, Floris P. J. T.
Udding, Jan H.
Hiemstra, Henk
Speckamp, W. Nico
The preparation of several a-fused 3-pyrazolidinones is described starting from 5,5-dimethyl-3-pyrazolidinone and using an acid-induced cyclization of a ?-nucleophile tethered to N-1 onto a cationic carbon bonded to N-2 (an exocyclic N-acylhydrazonium intermediate).The cyclization reactions proceed best with activated ?-nucleophiles such as allyl- and propargylsilanes.In the case of an ester substituent at the cationic carbon, structural analogues of antibacterial bicyclic pyrazolidinones are obtained.The stereochemistry of one product is established by X-ray crystallographic analysis.Two cyclization products showed NMR spectra with very broad signals due to relatively high nitrogen-inversion barriers (ca. 13 kcal/mole).
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