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

Abstract:

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.

References:

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