Feasibility of sigmatropic rearrangement on electron-deficient coumarinyl ketones

LN Dutta, B De, G Pal, A Patra

Index: Dutta, Lakshmi Narayan; De, Banani; Pal, Godhuli; Patra, Amarendra Canadian Journal of Chemistry, 2008 , vol. 86, # 5 p. 401 - 409

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Abstract

Different alkyl/aryl 7-hydroxy-8-coumarinyl ketones were converted to 7-O-allyl and 7-O- cyclohexenyl ethers and the study of hitherto unreported sigmatropic rearrangement on 7-O- allyl and 7-O-cyclohex-2'-ene-1'-ylcoumarinyl ketones prepared is accounted herein. The rearrangement yielded alkyl/aryl 6-allyl-7-hydroxy-8-coumarinyl ketones 3 and alkyl/aryl 6- cyclohex-2'-en-1'-yl-7-hydroxy-8-coumarinyl ketones 7 as the major products. Interestingly ...