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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

Email: nooruddin401@gmail.com



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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2. R.J.Whikhom and H.W.Moore, J.Am.Chem.Soc. 94, 6152, (1972).