Syntheses of Imidazo-, Oxa-, and Thiazepine Ring Systems via Ring-Opening of Aziridines/Cu-Catalyzed C-N/C-C Bond Formation

被引：47

作者：

Ghorai, Manas K. ^{[1
]}

Sahoo, Ashis Kumar ^{[1
]}

Bhattacharyya, Aditya ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 14期

关键词：

DEHYDROGENATIVE-COUPLING REACTION; ELECTRON-WITHDRAWING GROUPS; N-ACTIVATED AZIRIDINES; ENANTIOSELECTIVE SYNTHESIS; MESO-AZIRIDINES; NITROGEN ATOM; ARYL HALIDES; STEREOCONTROLLED SYNTHESIS; ANTICANCER ACTIVITY; EFFICIENT APPROACH;

D O I：

10.1021/jo500888j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and unpredicted synthetic pathway toward racemic and scalemic tetrahydrodibenzoimidazoazepines has been invented serendipitously proceeding through an S(N)2-type ring-opening of N-activated aziridines with 2-bromobenzylamine followed by a hitherto unprecedented cascade cyclization reaction sequence comprising a Cu-catalyzed cross dehydrogenation C-N coupling and an Ullmann C-C bond formation reaction. The tetrahydrobenzoxazepine and the tetrahydrobenzothiazepine derivatives have also been synthesized via the ring-opening of aziridines with 2-bromobenzyl alcohols and -mercaptan, respectively, followed by Cu-catalyzed N-arylation reaction.

引用

页码：6468 / 6479

页数：12

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