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

页码：452 / 462

页数：11

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