Department of Chemistry, Indian Institute of Technology Bombay , Mumbai 400 076, India.
Org Lett. 2017 Aug 18;19(16):4283-4286. doi: 10.1021/acs.orglett.7b01924. Epub 2017 Aug 2.
The Hauser-Kraus reaction of sulfonyl phthalide with nitroalkene derivatives provides access to aminophenanthrenes, including phenanthrene-substituted amino acids and benzoquinolines. The intermediate quinones bearing a key ketoalkyl moiety undergoes facile intramolecular enamine cyclization. Interestingly, enamines derived from primary and secondary amines undergo cyclization via C-centered nucleophilic attack to provide aminophenanthrenes, whereas those derived from ammonia undergo cyclization via N-centered nucleophilic attack leading to benzoquinolines. A one-pot protocol for the direct transformation of phthalides and nitroalkene derivatives to aminophenanthrenes and benzoquinolines has also been developed.
磺酰基邻苯二甲酰亚胺与硝基烯烃衍生物的豪泽-克劳斯反应为氨基菲并[9,10-b]喹啉的合成提供了一种途径，包括菲并[9,10-b]氨基酸和苯并喹啉。带有关键酮烷基部分的中间体醌经历了易于发生的分子内烯胺环化。有趣的是，伯胺和仲胺衍生的烯胺通过 C 中心亲核进攻进行环化，提供氨基菲并[9,10-b]喹啉，而氨衍生的烯胺通过 N 中心亲核进攻进行环化，得到苯并喹啉。还开发了一种将邻苯二甲酸酐和硝基烯烃衍生物直接转化为氨基菲并[9,10-b]喹啉和苯并喹啉的一锅法。
