Syntheses of Imidazo-, Oxa-, and Thiazepine Ring Systems via Ring-Opening of Aziridines/Cu-Catalyzed C鈥揘/C鈥揅 Bond Formation
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- 作者：Manas K. Ghorai ; Ashis Kumar Sahoo ; Aditya Bhattacharyya
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：July 18, 2014
- 年：2014
- 卷：79
- 期：14
- 页码：6468-6479
- 全文大小：603K
- ISSN：1520-6904
文摘
A simple and unpredicted synthetic pathway toward racemic and scalemic tetrahydrodibenzoimidazoazepines has been invented serendipitously proceeding through an SN2-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鈥揘 coupling and an Ullmann C鈥揅 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.