One-Pot Procedure for the Synthesis of 1,5-Benzodiazepines from N-Allyl-2-bromoanilines

被引：30

作者：

Weers, Marco ^{[1
]}

Luehning, Lars H. ^{[1
]}

Luehrs, Vanessa ^{[1
]}

Brahms, Christian ^{[1
]}

Doye, Sven ^{[1
]}

机构：

[1] Carl von Ossietzky Univ Oldenburg, Inst Chem, Carl von Ossietzky Str 9-11, D-26111 Oldenburg, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 06期

关键词：

amination; amines; benzodiazepines; palladium; titanium; H BOND ACTIVATION; TITANIUM-CATALYZED HYDROAMINOALKYLATION; INTERMOLECULAR HYDROAMINOALKYLATION; C-N; INTRAMOLECULAR HYDROAMINOALKYLATION; UNACTIVATED OLEFINS; TANTALUM COMPLEXES; AMIDATE COMPLEXES; ALPHA-ALKYLATION; SECONDARY-AMINES;

D O I：

10.1002/chem.201604561

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new one-pot procedure that includes an initial titanium-catalyzed intermolecular hydroaminoalkylation of N-allyl-2-bromoanilines with N-methylanilines and a subsequent intramolecular Buchwald-Hartwig amination directly gives access to pharmacologically relevant 1,5-benzodiazepines. The process takes advantage of the excellent regioselectivity of the initial hydroaminoalkylation performed in the presence of a titanium mono(formamidinate) catalyst and the fact that the exclusively formed branched hydroaminoalkylation products can only undergo palladium-catalyzed cyclization to 1,5-benzodiazepines.

引用

页码：1237 / 1240

页数：4

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