Aluminum-Catalyzed Cross Selective C3-N1′ Coupling Reactions of N-Methoxyindoles with Indoles

被引：2
|
作者：
Tokushige, Keisuke [1 ]
Yamashiro, Toshiki [1 ]
Hirao, Seiya [1 ]
Abe, Takumi [1 ]
机构：
[1] Okayama Univ, Grad Sch Med Dent & Pharmaceut Sci, Okayama 7008530, Japan
来源：
CHEMISTRY-SWITZERLAND | 2023年 / 5卷 / 01期
关键词：
1 ' H-1,3 '-biindole; N-electrophilic; N-methoxyindoles; bisindoles; aluminum; cross-coupling; NUCLEOPHILIC-SUBSTITUTION REACTION; ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; FUNCTIONALIZATION; 1-HYDROXYINDOLES; CHEMISTRY; NITROGEN; NUCLEUS; ROUTE; METAL;
D O I：
10.3390/chemistry5010033
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
C3-N1 ' bond formation of bisindoles has been a great challenge due to the intrinsic reactivity of indoles as both C3 and N1-nucleophilic character. Herein, we demonstrate an C3-N1 ' cross-coupling reaction of indoles using N-methoxyindoles as N-electrophilic indole reagents in the presence of Lewis acid. The bisindoles generated in this transformation are latent C3-nucleophile, allowing them to be used as strategic intermediates in sequential C3-N1 '-C3 '-N1 '' triindole formations. The potential synthetic usefulness of this sequential transformation was highlighted upon application to the construction of C3-N1 looped polyindoles.
引用
收藏
页码：452 / 462
页数：11
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