Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry (Tianjin Normal University), Ministry of Education, College of Chemistry , Tianjin Normal University , Tianjin 300387 , People's Republic of China.
Org Lett. 2018 Sep 21;20(18):5680-5683. doi: 10.1021/acs.orglett.8b02406. Epub 2018 Sep 6.
A dramatic N-substituent controlled tandem annulation of 2-(2-(2-bromoethyl)phenyl)-1-sulfonylaziridines with 1,3-dicarbonyl compounds has been developed. When the N-substituent was a 4-methylbenzenesulfonyl group (Ts), sequential ring opening of aziridines, nucleophilic substitution, and lactamization took place to provide a series of hexahydrobenz[ e]isoindole compounds in good yields with good diastereoselectivities. By contrast, 3-benzazepine compounds were afforded in good yields via ring opening of aziridines and nucleophilic substitution when the N-substituent was the 4-nitrobenzenesulfonyl group (Ns).
已开发出一种具有 2-(2-(2-溴乙基)苯基)-1-磺酰基氮丙啶与 1,3-二羰基化合物的剧烈 N-取代基控制串联环化反应。当 N-取代基为对甲苯磺酰基（Ts）时，氮丙啶的顺序开环、亲核取代和内酰胺化发生，以良好的收率和良好的非对映选择性提供了一系列六氢苯并[e]异吲哚化合物。相比之下，当 N-取代基为 4-硝基苯磺酰基（Ns）时，通过氮丙啶的开环和亲核取代反应得到了 3-苯并氮杂卓化合物，产率良好。
