期刊
ORGANIC LETTERS
卷 19, 期 16, 页码 4283-4286出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01924
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资金
- SERB-DST India
- CSIR India
The HauserKraus 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.
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