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
收藏
页码：1237 / 1240
页数：4
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