Bronsted Acid Catalyzed Cyclization of Inert N-Substituted Pyrroles to Benzo[f]pyrrolo[1,2-a][1,4]diazepines

被引：3
|
作者：
Gao, Zeng [1 ,2 ]
Qian, Jinlong [1 ]
Yang, Huameng [1 ]
Zhang, Jinlong [1 ]
Jiang, Gaoxi [1 ]
机构：
[1] Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat, Ctr Excellence Mol Synth, Suzhou Res Inst LICP,Lanzhou Inst Chem Phys LICP, Lanzhou 730000, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
SYNLETT | 2021年 / 32卷 / 09期
基金：
中国国家自然科学基金;
关键词：
Bronsted acid catalysis; cyclization; pyrroles; intermolecular addition; azepines; asymmetric catalysis;
D O I：
10.1055/a-1468-5725
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two approaches involving intramolecular and intermolecular cyclization, respectively, have been developed for the direct and practical construction of a series of important benzo[f]pyrrolo[1,2a][1,4]azepines by using Bronsted acid catalysts. Upon catalysis by TsOH, the intramolecular dehydroxylation/ring closure of 3-hydroxy-2[2-(1H-pyrrol-1-yl)benzyl]isoindolin-1-ones provided various racemic benzo[f]pyrrolo[1,2-a][1,4]azepines in high yields. Furthermore, enantioenriched benzo[f]pyrrolo[1,2-a][1,4]azepines were also obtained by chiral phosphoric acid catalyzed intermolecular addition of [2-(1H-pyrrol-1-yl)phenyl]methanamines to 2-formylbenzoates under mild conditions.
引用
收藏
页码：930 / 934
页数：5
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