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

页码：930 / 934

页数：5

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