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 journalArticle

Abstract

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
Volume93
Issue number8
DOIs
Publication statusPublished - Aug 2020

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Fingerprint Dive into the research topics of 'N-acylcarbazole as a selective transamidation reagent'. Together they form a unique fingerprint.

Cite this