N-Acylcarbazole as a Selective Transamidation Reagent
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 addit...
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| Veröffentlicht in: | Bulletin of the Chemical Society of Japan 2020-08, Vol.93 (8), p.993-999 |
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| container_title | Bulletin of the Chemical Society of Japan |
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| creator | Kang, Bubwoong Yasuno, Yoko Okamura, Hironori Sakai, Asumi Satoh, Tetsuya Kuse, Masaki Shinada, Tetsuro |
| description | 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. |
| doi_str_mv | 10.1246/bcsj.20200116 |
| format | Article |
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| ispartof | Bulletin of the Chemical Society of Japan, 2020-08, Vol.93 (8), p.993-999 |
| issn | 0009-2673 1348-0634 |
| language | eng |
| recordid | cdi_proquest_journals_2439407684 |
| source | Oxford University Press Journals All Titles (1996-Current) |
| subjects | Acetylation Acylation Additives Amines Aniline Carbazoles Chemical synthesis Functional groups Natural products Polyamines Reagents Selectivity |
| title | N-Acylcarbazole as a Selective Transamidation Reagent |
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