期刊
CHEMISTRYSELECT
卷 7, 期 23, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.202201709
关键词
Dearomatization reaction; Heterocycles; Michael addition; Ritter reaction; Sulfuric Acid
资金
- [122012500098-4]
A method for rapidly constructing indolo[3,2-l]acridin-7-one systems bearing an isocryptolepine scaffold is described. The method involves a metal-free condensation reaction in concentrated sulfuric acid, resulting in the formation of polyannulated compounds with four new stereogenic centers in a highly diastereoselective manner. The reaction includes elecrophilic dearomatization of a methoxyarene, formation of a spirocyclic intermediate, and an intramolecular 1,4-nucleophilic addition sequence.
A method for rapid construction of indolo[3,2-l]acridin-7-one systems bearing isocryptolepine scaffold is described. Metal-free condensation of (4-methoxyphenyl)cyclohexan carbinols with ortho-amino/hydroxybenzonitriles in concentrated sulfuric acid yields polyannulated compounds with four new stereogenic centers in a highly diastereoselective manner. The reaction includes elecrophilic dearomatization of methoxyarene, formation of spirocyclic intermediate and intramolecular 1,4-nucleophilic addition sequence.
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