1. FeCl -Promoted ring size-dictating diversity-oriented synthesis (DOS) of N-heterocycles using -generated cyclic imines and enamines
- Author
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Dhandabani, Ganesh Kumar, Mutra, Mohana Reddy, and Wang, Jeh-Jeng
- Subjects
010405 organic chemistry ,Chemistry ,Metals and Alloys ,Aromatization ,Cyclohexanone ,Regioselectivity ,General Chemistry ,Alkylation ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Medicinal chemistry ,Catalysis ,0104 chemical sciences ,Surfaces, Coatings and Films ,Electronic, Optical and Magnetic Materials ,Ring size ,chemistry.chemical_compound ,Nucleophile ,Acridine ,Materials Chemistry ,Ceramics and Composites - Abstract
The FeCl -promoted ring size-controlled oxidative activation of -alkynylanilines opens up a complementary appealing protocol for poly-N-heterocycle synthesis., The FeCl -promoted ring size-controlled oxidative activation of -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- -dig cyclization to afford the corresponding dibenzo[ , ][1,10]phenanthrolines and 12-benzoylated dihydrobenzo[ ]acridine skeletons. Later, these acridine motifs become completely unsaturated due to dehydrogenative aromatization the aza-allyl oxidation intermediate. We obtained all quaternary carbon centre pseudoindoxyls through the Mannich-type alkylation of 2,3-dihydro-1 -inden-1-one with cyclic ketimines generated from the intramolecular nucleophilic cyclization of -alkynylanilines.
- Published
- 2019
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