Preparation and reactions of 4-(trimethylsilyl) indole

D Dauzonne, IA O'Neil, A Renaud

Index: Barrett, Anthony G. M.; Dauzonne, Daniel; O'Neil, Ian A.; Renaud, Alain Journal of Organic Chemistry, 1984 , vol. 49, # 23 p. 4409 - 4415

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Citation Number: 30

Abstract

Indole or 1-(trimethylsily1) indole was reacted sequentially with lithium-chlorotrimethylsilane and with 1, 4-benzoquinone to produce 1, 4-bis (trimethylsilyl) indole (50% and 55%, respectively). Methanolysis gave 4-(trimethylsily1) indole which reacted with electrophiles at C-3. However, the derivative l-acetyl-4-(trimethylsily1) indole reacted with acetyl, 2- chloropropanoyl, or propenoyl chlorides via clean C-4 ipso substitution. Attempts to ...