Convenient preparation of indolyl Malonates via Carbenoid insertion |
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Authors: | Gibe Romelo Kerr Michael A |
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Institution: | Department of Chemistry, The University of Western Ontario, London, Ontario, Canada. |
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Abstract: | Indoles, when treated with methyldiazomalonate under catalysis by rhodium(II)acetate, undergo C-H and N-H insertion reactions regioselectively depending on the substitution pattern on the indole moiety. In indoles where the 3-position is unsubstituted, high yields of the C3-H insertion product were observed. In 3-alkylindoles, 2-substitution predominated, while N-methyltetrahydrocarbazole yielded the product resulting from insertion into the C6-H bond. Indoles in which the nitrogen is unprotected yield varying degrees of N-H insertion. |
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