Title:Sodium Carbonate Sesquiperhydrate (2Na2CO3-3H2O2) Catalysed One-pot Synthesis of Biologically Dynamic Novel Substituted Spirooxirane Dicarboxamides
VOLUME: 1 ISSUE: 3
Author(s):Anshu Dandia, Ashok Kumar Laxkar and Sumit Bhaskaran
Affiliation:Centre of Advanced Studies, Department of Chemistry, University of Rajasthan, Jaipur-302004 India.
Keywords:Epoxidation, spirooxindole, Knoevenagel adduct, geminal dicyano functionality, sodium hypochlorite, rhodium(II)acetate catalyst, trichloroisocyanuric acid, dimethyldioxirane, peptide hydrolase inhibitors, scaffold, melanoma, Na2CO3, column chromatography, mechanistic pathway, malononitrile
Abstract:Sodium carbonate sesquiperhydrate catalyzed efficient one-pot synthesis of novel spiro[indoline-3,2'-
oxirane]dicarboxamides was achieved via Knoevenagel adduct of isatin with malononitrile as the key step followed by a
sequential tandem reaction. The Knoevenagel adduct transpires into oxirane with the geminal dicyano functionality being
hydrolysed in to corresponding dicarboxamide. Further extension of the scope of reaction with various other cyclic ketone
such as 9H-fluoren-9-one, 1H-indene-1,2,3-trione and cycloheptanone was found to be equally feasible as well as efficient,
rendering the final spiro compounds in good yields. This method has the advantages of short synthetic route, operational
simplicity, shorter reaction times, for small scale high-speed synthesis and is environmentally benign. The structure
elucidation and attribution of relative stereochemistry were unequivocally determined by X-ray structural analysis.
