Synthesis of 3,3-dimethoxy-2-aryl-2,3-dihydro-1-oxa-cyclopenta[l]phenanthren-2-ols and their conversion to 2(3H)- and 3(2H)-furanones |
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Authors: | Ambily M Jacob |
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Institution: | Department of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India |
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Abstract: | A number of new 3,3-dimethoxy-2-aryl-2,3-dihydro-1-oxacyclopental]phenanthren-2-ols were synthesized by the base-catalyzed reaction between phenanthrenequinone and 4-substituted acetophenones in methanol. These furanols are unstable and are easily converted to stable 3-methoxy-3-aryl-3H-1-oxacyclopental]phenathren-2-ones in excellent yields. The furanols are converted to 2-aryl-1-oxacyclopental]phenanthren-3-ones on treatment with acids. Plausible mechanisms for some of these new transformations are proposed. |
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Keywords: | Furanol Furanone Phenanthrenequinone Rearrangement |
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