<i>N</i>-Acylcarbazole as a Selective Transamidation Reagent

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Author(s)

Abstract

<p><i>N</i>-acylation reaction offers an opportunity to develop an efficient synthesis of amide group-containing molecules. We found that <i>N</i>-acyl carbazoles showed remarkable selectivity in transamidation. Sterically less hindered primary amines are selectively acylated with <i>N</i>-acyl carbazoles without any additives. Various functional groups such as alcohol, phenol, indole, and aniline moieties are tolerated under mild conditions. The synthetic utility was displayed in one-pot synthesis of an <i>N</i>-acyl polyamine natural product. The terminal amines of spermidine were selectively benzoylated with <i>N</i>-benzoyl carbazole, followed by acetylation reaction accomplished the total synthesis in a highly efficient manner.</p>

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 93(8), 993-999, 2020

    The Chemical Society of Japan

Codes

  • NII Article ID (NAID)
    130007888018
  • Text Lang
    ENG
  • ISSN
    0009-2673
  • Data Source
    J-STAGE 
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