Indole syntheses utilizing o-methylphenyl isocyanides.
Y Ito, K Kobayashi, N Seko, T Saegusa
Index: Ito; Kobayashi; Seko; Saegusa Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 1 p. 73 - 84
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Citation Number: 61
Abstract
New indole synthesis starting with o-methylphenyl isocyanides such as o-tolyl, 2, 4-xylyl, and 2, 6-xylyl isocyanide is described in full detail. Treatment of o-tolyl isocyanide with LDA in diglyme at− 78° C generated selectively o-(lithiomethyl) phenyl isocyanide in an almost quantitative yield, which on warming up to room temperature was cyclized to indole after aqueous workup. Similary, 2, 4-xylyl and 2, 6-xylyl isocyanides were cyclized to 5- ...
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