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2004
Dioxane derivatives
R 0470
Efficient Synthesis of 2- and 3-Substituted-2,3-dihydro[1,4]dioxino[2,3-b]pyridine
— A convenient strategy for the synthesis of 2- and 3-substituted47- 136 Derivatives.
-2,3-dihydropyridines is reported. While 3-substituted derivatives like (II) are obtained
by classical nucleophilic aromatic substitution, the access to the corresponding 2-substituted derivatives is realized via Smiles rearrangement. A study of conditions affecting this rearrangement is carried out by varying parameters such as nucleofuge, base
and solvent. It is found that the Smiles rearrangement is facilitated by activation of the
aromatic ring by electron-withdrawing groups (like nitro-group) in the ortho-position.
— (LAZAR, S.; SOUKRI, M.; LEGER, J. M.; JARRY, C.; AKSSIRA, M.; CHIRITA,
R.; GRIG-ALEXA, I. C.; FINARU, A.; GUILLAUMET*, G.; Tetrahedron 60 (2004)
31, 6461-6473; Inst. Chim. Org. Anal., CNRS, Fac. Sci., Univ. Orleans,
F-45067 Orleans, Fr.; Eng.) — Bartels
2004
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