3,3'-[Diselenobis(methylene)]bis[5-hydroxy-6-methyl-4-pyridinemethanol

The intermediate 3 was synthesized utilizing the methodology of Deng [1]. A mixture of 3 (3.4g, 14mmol) in 60ml of H₂O was stirred at 60-65deg.C for 1.4h and cooled to room temperature. Then 25ml of Na₂Se₂ solution (19mmol) was added dropwise. After adjustment to pH 8, the mixture was stirred at 60deg.C for 2h and cooled to room temperature. The precipitate was filtered off and washed with water. The solid was solved in 20ml of 10% HCl, and stirred for 0.5h, filtered and washed with 10% HCl. The mother liquor was adjusted to pH 8 with 40% NaOH to give a precipitate which was filtered off and washed with water. Yellow solid 3,3′-[diselenobis(methylene)]bis[5-hydroxy-6-methyl-4-pyridine-methanol (1) 2.5g (77.3%). Mp:192-3deg.C.

IR(KBr) n (cm^-1): 3100 (-OH), 2706, 2628, 1560, 1405, 1236, 1039, 772, 716.

¹H-NMR (DMSO-d6) dH (ppm): 2.32 (s, 6H, -CH₃), 3.98 (s, 4H, -CH₂Se-), 4.75 (s, 4H, -CH₂O), 7.70 (s, 2H, H-2).

MS (m/z,%): 462 (M⁺, 2%) 231, 213, 152, 136, 122, 106, 94, 77, 66, 53, 39 (100%).

Anal.(C₁₆H₂₀N₂Se₂O₄) C, H, N.

Acknowledgment: This research was supported by the Natural Sciences Foundation of Guangdong Province.