One-Pot Conversion of 1-Bromo-β-carboline and 1-Bromocarbazole into Pentacyclic Compounds by Suzuki Cross-Coupling Followed by Spontaneous Cyclization

被引：8

作者：

Gehring, Andre P. ^{[1
]}

Tremmel, Tim ^{[1
]}

Bracher, Franz ^{[1
]}

机构：

[1] Univ Munich, Ctr Drug Res, Dept Pharm, D-81377 Munich, Germany

来源：

SYNTHESIS-STUTTGART | 2014年 / 46卷 / 07期

关键词：

cross-coupling; canthines; beta-carbolines; carbazoles; oxidative cyclization; RING-SYSTEM; ALKALOID ASCIDIDEMIN; AROMATIC ALKALOIDS; ANALOGS; CANTHIN-4-ONE; ARYLATION; ROUTE;

D O I：

10.1055/s-0033-1338591

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This work describes a straightforward one-pot conversion of 1-bromo-beta-carboline and 1-bromocarbazole into pentacyclic compounds. Suzuki cross-coupling with various 2-methoxycarbonylphenylboronic acids was followed by spontaneous lactamization to give the target products. Coupling of 1-bromo-beta-carboline with 2-formylphenylboronic acid also gave the oxo product through oxidative cyclization, whereas in the carbazole series, the intermediate hemiaminals undergo a disproportionation reaction to give both the oxo and the methylene product.

引用

页码：893 / 898

页数：6

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