Dimethyl sulphoxide as a reagent brings about N-methylthiomethylation and N,N/-methyl -thiomethylation in substituted barbituric acids. It converts 4-acetoxy coumarins to corresponding ylides and brings about methylene insertion in 1,6-naphtharidenes at reflux temperature.DMSO activated by trifluoro-aceticanhydride brings about formation of mono, bis and tris-sulphonic substituted derivatives when interacted with cyclo pentadiene and trimethylsilyl cyclopentadiene.This reagent converts 3-Nitro-4-hydroxy coumarins to salicylic acid in dichloromethane at low temperature.DMSO-acetic anhydride reagent converts enols to sulphur ylides, introduces methylthiomethyl group into phenols and oxidizes secondary alcohols to corresponding ketones. It brings about oxidative rearrangement in polyporic acid and converts 4-hydroxy coumarins and its 3-substituted derivatives into a wide range of products under different conditions.DMSO-SO3 pyridine complex in presence of triethyl amine oxidizes cis-diols to corresponding quinones.DMSO-activated by N-bromosuccinimide brings about methylation of alcohols and converts diols to their corresponding methylene-acetals.
Dimethyl sulphoxide as a reagent brings about N-methylthiomethylation and N,N/-methyl -thiomethylation in substituted barbituric acids. It converts 4-acetoxy coumarins to corresponding ylides and brings about methylene insertion in 1,6-naphtharidenes at reflux temperature.DMSO activated by trifluoro-aceticanhydride brings about formation of mono, bis and tris-sulphonic substituted derivatives when interacted with cyclo pentadiene and trimethylsilyl cyclopentadiene.This reagent converts 3-Nitro-4-hydroxy coumarins to salicylic acid in dichloromethane at low temperature.DMSO-acetic anhydride reagent converts enols to sulphur ylides, introduces methylthiomethyl group into phenols and oxidizes secondary alcohols to corresponding ketones. It brings about oxidative rearrangement in polyporic acid and converts 4-hydroxy coumarins and its 3-substituted derivatives into a wide range of products under different conditions.DMSO-SO3 pyridine complex in presence of triethyl amine oxidizes cis-diols to corresponding quinones.DMSO-activated by N-bromosuccinimide brings about methylation of alcohols and converts diols to their corresponding methylene-acetals.
Nitrogen heterocycles have played an important role in different industrial sectors.Porphyrins the macrocyclic compounds containing pyrrole rings provide an extremely versatile platform with desired peripheral functionality and metal complexes to form the self assembly under varying reaction conditions. Haemoglobin an iron complex is responsible for binding molecular oxygen and transporting it to different sites. Mechanistically interesting N-heterocycles, Arylidene-1,3-indandione adducts (6) and (7) synthesized frequently are of immense pharmaceutical importance showing fungicidal and bactericidal activities. Nitrogen heteroatom phthalimide derivatives(8),(9) and (10) have been evaluated as possible potential prodrugs. A wide range of Nitrogen heterocycles have been synthesized for every imaginable use in dye and polymer industries.
DMSO/Ac 2 O reagent converts 1,3-indandione (1) to an unusual dimer 1H,1′H-2,2′-biindene-1,1′,3,3′(2H,2′H) tetrone and a dimeric condensation product along with an ylide (1a) at room temperature. This reagent also brings about oxidation of secondary alcohols to corresponding ketones, methyl thiomethylation, and N-hydroxymethylation in phthalimide and converts 4-hydroxycoumarins and dicoumarol to different oxidative and degradation products under varying conditions. However, when 1,3-indandione was refluxed with DMSO/Ac 2 O reagent at 150°C, it afforded a novel compound, 2-spiroindan 1,3-dione (2) , a Diels Alder Adduct, analogous to (3) obtained upon treatment of 1,3-indandione with formaldehyde in presence of primary amines.
Dimethyl Sulphoxide-acetic anhydride reagent converts 1,3-indandione to the ylide (2) and a much awaited dimer (3) at room temperature. However , when 1,3-indandione was interacted with pre- heated DMSO-acetic anhydride at waterbath temperature it affords an unusual trimer (4) and a novel compound (5), methine-tris-1,3-indandione along with the ylide (2) Key words: DMSO, Acetic anhydride, Indandione,Ylide Trimer.
Dimethyl sulphoxide activated by acetic-anhydride introduces methylthiomethyl group into phenols,oxidises certain medicinally useful secondary alcohols to their corresponding ketones and brings about oxidative rearrangements in different substrates.It converts 4-hydroxy coumarins and dicoumarols,under varying conditions,to a variety of products of both pharmaceutical and mechanistic interest.
When1,3-indandione (1) was interacted with this versatile reagent at water bath temperature,it afforded an ylide (2) and an oxidative cyclisation product (3).However,its interaction with Ar –CH = (CN)R,leads to the formation of a mechanistically interesting compound,indeno[1,2-b]-4H pyran(4).
DMSO alone has been used as a reagent and yields a number of products of mechanistic interest with different substrates.When 1,3-indandione (1) was refluxed with DMSO alone at elevated temperature,it results the formation of poly(methylene-bis) 1,3-indandione(5) involving methylene group insertion between different 1,3-indandione moieties.Methylene insertion has also been observed when 1,3-indandione (1) was condensed with formaldehyde in presence of alkali carbonates or primary amines to yield (6)and(7) respectively.
N- Methyl thiomethyl phthalimide (I) a new compound was obtained when phthalimide was refluxed with DMSO acetic anhydride reagent and DMSO alone at 180 o C. A different route for the synthesis of N- Hydroxy methylphthalilmide (II)with excellent yield has also been explored by this reaction. Key Words : DMSO, Acetic anhydride, Phthalimide, Methyl thiomethylation
Dimethyl sulphoxide reagent brings about N-methyl thiomethylation and N-hydroxy methylation in phthalimide at elevated temperature. It also converts 5,5-disubstituted barbituric acid to its N-methyl thiomethyl and N,N/-methyl thiomethyl derivatives at reflux temperature. A convenient and efficient procedure for the synthesis of poly(methylene-bis)-1,3-indandione derivative (2) was developed by one-pot reaction of 1,3-indandione (1) when refluxed with DMSO at 180°C . This provides an alternate method of mechanistic interest for the synthesis of tetrad (2) with excellent yield. The condensation product (2) can act as a basic unit for the synthesis of a polymer.
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