- Synthesis of new compounds containing the 2,3-dihydro[1,4]dioxino[2,3-b]pyridine heterocyclic system as a substructure
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2,3-Dihydro-spiro[1,4]dioxino[2,3-b]pyridine-3,3′-pyrrolidine (8A) and 2,3-dihydro-spiro[1,4]dioxino[2,3-b]pyridine-3,4′-piperidine (9A) have been synthesized from 2-chloro-3-pyridinol. The corresponding 2,3′ (8B) and 2,4′ (9B) isomers were obtained via the Smiles rearrangement, while 9B was also selectively synthesized from 2-nitro-3-pyridinol. The separation of the isomers A and B under the sulfamide form was carried out by flash column chromatography. Subsequent transformations of the corresponding dioxinopyridine derivatives were described.
- Soukri,Lazar,Pujol,Akssira,Leger,Jarry,Guillaumet
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- Regioselective synthesis of 2,3-dihydrospiro[1,4]dioxino[2,3-b]pyridine derivatives
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2-Chloropyridines and an aryl bromide underwent palladium-catalyzed intramolecular C-O bond forming reactions to provide 2,3-dihydrospiro[1,4] dioxino[2,3-b]pyridine derivatives and a benzodioxin, regioselectively.
- Tony, Kurissery A.,Chittimalla, Santhosh Kumar,Abraham Rajkumar,Chakrabarti, Anjan
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experimental part
p. 4350 - 4353
(2010/09/12)
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