Synthesis of new compounds containing the 2,3-dihydro[1,4]dioxino[2,3-b]pyridine heterocyclic system as a substructure
2003; Elsevier BV; Volume: 59; Issue: 20 Linguagem: Inglês
10.1016/s0040-4020(03)00513-1
ISSN1464-5416
AutoresMustapha Soukri, Saïd Lazar, M. Dolors Pujol, Mohamed Akssira, J.-M. Léger, C. Jarry, Gérald Guillaumet,
Tópico(s)Synthesis and Reactivity of Heterocycles
Resumo2,3-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.
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