Synthesis of 3,4,5-trisubstituted indoles via iterative directed lithiation of 1-(triisopropylsilyl)gramines |
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Authors: | Tsutomu Fukuda |
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Institution: | Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan |
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Abstract: | Directed lithiation of 1-(triisopropylsilyl)gramines 1 with tert-butyllithium followed by reaction with trimethylsilylmethyl azide produced 4-amino-1-(triisopropylsilyl)gramines 7. The N-tert-butoxycarbonyl derivatives 8 were lithiated selectively at C-5 with tert-butyllithium and the lithiated species were reacted with a variety of electrophiles to give 5-functionalized compounds, 9 and 10. A facile method to produce 3,4,5-trisubstituted indoles from readily available gramine derivatives is thereby established. |
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Keywords: | 1-(Triisopropylsilyl)gramines tert-Butyllithium Lithiation |
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