Direct N- and C-alkenylation of nitrogen-containing heterocycles with magnesium alkylidene carbenoids |
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Authors: | Jo Sakurada |
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Affiliation: | Department of Chemistry, Faculty of Science, Tokyo University of Science, Ichigaya-funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan |
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Abstract: | Treatment of magnesium alkylidene carbenoids, which were generated from 1-chlorovinyl p-tolyl sulfoxides with isopropylmagnesium chloride at −78 °C in toluene, with N-lithio nitrogen-containing heterocycles gave N-alkenylated products in moderate to good yields. Also, the reaction of C-lithio indoles, which were generated from N-protected indoles, with magnesium alkylidene carbenoids gave C-2 or C-3 alkenylated products, corresponding to the protective group. The intermediate of these reactions were found to be the alkenyl anion, which could be trapped with electrophiles to give the heterocycles having fully substituted alkenes. |
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Keywords: | Sulfoxide-magnesium exchange reaction Magnesium alkylidene carbenoid Alkenylation N-Alkenylation of heterocycles C-Alkenylation of heterocycles |
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