Tin-free radical cyclizations for the synthesis of 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b] azepin-8-ones

Eric Bacqué 1 Myriem El Qacemi 2 Samir Zard 2
1 AVENTIS Pharma
2 DCSO - Laboratoire de synthèse organique
Abstract : (Chemical Equation Presented) Compounds containing a pyridine nucleus fused to a saturated nitrogen-containing ring, including 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b] azepin-8-ones, were prepared in good yield starting from various 2,6-dichloropyridines. The method hinges on a free-radical xanthate-mediated cyclization or intermolecular addition/cyclization sequence for the construction of the new fused rings.
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Submitted on : Monday, March 24, 2014 - 1:24:10 PM
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Eric Bacqué, Myriem El Qacemi, Samir Zard. Tin-free radical cyclizations for the synthesis of 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b] azepin-8-ones. Organic Letters, American Chemical Society, 2004, 6 (21), pp.3671-3674. ⟨10.1021/ol0489649⟩. ⟨hal-00954818⟩

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