N-acylcarbazole as a selective transamidation reagent

Bubwoong Kang, Yoko Yasuno, Hironori Okamura, Asumi Sakai, Tetsuya Satoh, Masaki Kuse, Tetsuro Shinada

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)


N-acylation reaction offers an opportunity to develop an efficient synthesis of amide group-containing molecules. We found that N-acyl carbazoles showed remarkable selectivity in transamidation. Sterically less hindered primary amines are selectively acylated with N-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 N-acyl polyamine natural product. The terminal amines of spermidine were selectively benzoylated with N-benzoyl carbazole, followed by acetylation reaction accomplished the total synthesis in a highly efficient manner.

Original languageEnglish
Pages (from-to)993-999
Number of pages7
JournalBulletin of the Chemical Society of Japan
Issue number8
Publication statusPublished - Aug 2020
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)


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