Syntheses of spiro[cyclopropane-1,3′-oxindole]-2-carboxylic acid and cyclopropa[c]quinoline-7b-carboxylic acid and their derivatives |
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Authors: | Sarah R Yong Stephen G Pyne Brian W Skelton |
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Institution: | a Department of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia b Department of Chemistry, University of Western Australia, Crawley, Western Australia 6009, Australia |
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Abstract: | The synthesis of spirocyclopropane-1,3′-oxindole]-2-carboxylic acid, including novel 3-(2- and 3-pyridyl)-substituted analogues and the novel cyclopropac]quinoline-7b-carboxylic acid and their ester and amide derivatives is described. These syntheses involve diastereoselective cyclopropanation reactions of methyl 2-(2-nitrophenyl)acrylate and (3E)-(pyridin-2-ylmethylene)- and (3E)-(pyridin-3-ylmethylene)-1,3-dihydro-2H-indol-2-one with ethyl (dimethyl sulfuranylidene) acetate (EDSA). The synthesis of methyl cyclopropac]quinoline-7b-carboxylate involves a regioselective reductive cyclization of a nitro-diester precursor. The relative stereochemistry of key compounds has been determined by single-crystal X-ray structural analysis. |
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Keywords: | Cyclopropanation Sulfur ylide Spirocyclic compounds Oxindole Quinoline |
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