83188-12-9Relevant academic research and scientific papers
Preparation and Reactions of 4-(Trimethylsilyl)indole
Barrett, Anthony G. M.,Dauzonne, Daniel,O'Neil, Ian A.,Renaud, Alain
, p. 4409 - 4415 (2007/10/02)
Indole or 1-(trimethylsilyl)indole was reacted sequentially with lithium-chlorotrimethylsilane and with 1,4-benzoquinone to produce 1,4-bis(trimethylsilyl)indole (50 percent and 55 percent, respectively).Methanolysis gave 4-(trimethylsilyl)indole which reacted with electrophiles at C-3.However, the derivative 1-acetyl-4-(trimethylsilyl)indole reacted with acetyl, 2-chloropropanoyl, or propenoyl chlorides via clean C-4 ipso substitution.Attemps to extend the reaction to a useful synthesis of derivatives of 5-oxo-1,3,4,5-tetrahydrobenzindole, a lysergic acid synthon, were prevented by low yields.
