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A novel MgI2 mediated unusual dimerization-spirocyclopropanation of bromo isomerised Morita-Baylis-Hillman adduct of isatin: a facile synthesis of 3-spirocyclopropane-2-oxindole derivatives |
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| Authors: | Kandapalam Arun Prasath LingamAsit Baran Mandal Ponnusamy Shanmugam |
| Institution: | a Organic Chemistry Division, Central Leather Research Institute, Council of Scientific and Industrial Research (CSIR), Adyar, Chennai 600 020, India b Chemical Laboratory, Central Leather Research Institute, Council of Scientific and Industrial Research (CSIR), Adyar, Chennai 600 020, India |
| Abstract: | A novel magnesium iodide mediated unusual dimerization-spirocyclopropanation of bromo isomerised Morita-Baylis-Hillman adducts of isatin afforded highly functionalized 3-spirocyclopropane-2-oxindole derivatives as regioisomers in good combined yield. It has been observed that the regioselectivity is dependent on the nature of electron withdrawing group at the activated position. A plausible mechanism involving organomagnesium reagent has been proposed. |
| Keywords: | Isatin Magnesium iodide Morita-Baylis-Hillman adduct Spirocyclopropane-2-oxindole Dimerization-spirocyclopropanation |
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