Synthesis

One-pot synthesis of 2, 3-disubstituted N-tosylindoles from o-acyl-N-tosylanilines

Y Hari, T Kanie, T Miyagi, T Aoyama

Index: Hari, Yoshiyuki; Kanie, Tomoki; Miyagi, Takashi; Aoyama, Toyohiko Synthesis, 2006 , # 8 p. 1249 - 1252

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Citation Number: 6

Abstract

Very recently, we reported a new class of synthetic methods of 3-substituted N-tosylindoles 1 from o-acyl-N-tosylanilines 2 and the lithium salt of trimethylsilyldiazomethane [TMSC(Li)N 2 ] via the intramolecular N-Li insertion of the resulting alkylidenecarbene intermediates 3 (Scheme [1] ). [2] N-Protected indoles are well-known to generate their 2-lithio derivatives by treatment with a strong base such as n-BuLi, t-BuLi, or LDA, which easily react with electrophiles to ...

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