Unusual Knoevenagel condensations of 16a-substituted-16-methylene-17-keto-steroids |
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| Authors: | B Green I S Khaidem R I Crane S S Newaz |
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| Institution: | Department of Chemistry, University of Maine, Orono, Maine 04473, U.S.A. |
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| Abstract: | A Knoevenagel condensation between 3β-acetoxy-16-pyrrolidinylmethylenandrost-5-en-17-one (8c) and an excess of malononitrile led unexpectedly to 3β-acetoxyandrost-5-eno-17,16-c]-1′,6′-dicyanoaniline (12a) as the major product and 3β-acetoxy-16-pyrrolidinylmethylen-17-dicyanomethylenandrost-5-ene (11a) as the minor product. Knoevenagel reactions of other 16a-substituted-16-methylen-17-keto steroids were studied to evaluate the scope and mechanism of the reaction. |
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