Synthesis and characterisation of 1,3-indandione derivatives and related compounds
Noor-ud Din- Zargar and Khaliq-uzZaman-Khan
Department of Chemistry University of Kashmir Srinagar-190006(J&K) India
Dimethylsulphoxide-aceticanhydride reagent brings about oxidation of secondary alcohols to corresponding ketones, oxidative rearrangements, oxidative cyclisation and methylene-bis-adduct formation in different 1,3-diketo compounds. It converts 4-hydroxycoumarins and its 2-substituted derivatives, under varying conditions, to a variety of products of pharmaceutical and mechanistic interest. Interaction of this reagent with 1,3-indandione at room temperature affords an ylide(1), a dimer (2) and a dimeric condensation product (3) but at waterbath temperature it results an unusual trimer and a methine-tris-1,3-indandione derivative along with the ylide (1). However, when phthalimide was refluxed with DMSO/Ac2O reagent or DMSO alone, N-methyl-thiomethyl phthalimide and N-hydroxy methyl phthalimide were obtained in high yields.
Keywords: DMSO, Acetic-anhydride, Indandione, Ylide, Dimer, Trimer, Phthalimide.
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