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Updated: Jan 23, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
FeCl3-Promoted ring size-dictating diversity-oriented synthesis (DOS) of N-heterocycles using in situ-generated
Ganesh Kumar Dhandabani1, Mohana Reddy Mutra1, Jeh-Jeng Wang2
1Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, No. 100, Shiquan 1st Rd, Sanmin District, Kaohsiung City 807, Taiwan. jjwang@kmu.edu.tw.
Abstract:
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 π-alkyne iron species combine with cyclic enamines obtained from cyclohexanone and β-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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