期刊
CHEMICAL COMMUNICATIONS
卷 55, 期 52, 页码 7542-7545出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9cc03375k
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资金
- Ministry of Science and Technology (MOST), Taiwan
- Centre for Research and Development of Kaohsiung Medical University
The FeCl3-promoted ring size-controlled oxidative activation of o-alkynylanilines opens up a complementary appealing protocol for poly-N-heterocycle synthesis. When electron-poor pi-alkyne iron species combine with cyclic enamines obtained from cyclohexanone and beta-tetralone, they undergo a regioselective 6-exo-dig cyclization to afford the corresponding dibenzo[b,j][1,10]phenanthrolines and 12-benzoylated dihydrobenzo[a]acridine skeletons. Later, these acridine motifs become completely unsaturated due to dehydrogenative aromatization via the aza-allyl oxidation intermediate. We obtained all quaternary carbon centre pseudoindoxyls through the Mannich-type alkylation of 2,3-dihydro-1H-inden-1-one with cyclic ketimines generated from the in situ intramolecular nucleophilic cyclization of o-alkynylanilines.
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