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【结 构 式】

【分子编号】58431

【品名】7-hydroxy-4-methyl-2H-pyrano[2,3-b]pyridin-2-one

【CA登记号】

【 分 子 式 】C9H7NO3

【 分 子 量 】177.15952

【元素组成】C 61.02% H 3.98% N 7.91% O 27.09%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(I)

Condensation of 4-methyl-7-hydroxypyrano[2,3-b]pyridin-2-one (I) with N,N-dimethylthiocarbamoyl chloride gives the thiocarbamate (II), which undergoes thermal rearrangement at 220 C to the S-aryl thiocarbamate isomer (III). Subsequent alkaline hydrolysis of (III) provides the 7-mercapto azacoumarin (IV). Alkylation of (IV) with chloroacetone (V) affords thioether (VI). This compound is finally cyclized to the target pyranothienopyridine compound under alkaline conditions.

1 Via, L.D.; et al.; Synthesis, photobiological activity and photoreactivity of methyl-thieno-8-azacoumarins, novel bioisosters of psoralen. Bioorg Med Chem Lett 2002, 12, 9, 1253.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 58431 7-hydroxy-4-methyl-2H-pyrano[2,3-b]pyridin-2-one C9H7NO3 详情 详情
(II) 58432 O-(4-methyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl) dimethylcarbamothioate C12H12N2O3S 详情 详情
(III) 58433 S-(4-methyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl) dimethylcarbamothioate C12H12N2O3S 详情 详情
(IV) 58434 4-methyl-7-sulfanyl-2H-pyrano[2,3-b]pyridin-2-one C9H7NO2S 详情 详情
(V) 15288 1-Chloroacetone; Chloroacetone 78-95-5 C3H5ClO 详情 详情
(VI) 58435 4-methyl-7-[(2-oxopropyl)sulfanyl]-2H-pyrano[2,3-b]pyridin-2-one C12H11NO3S 详情 详情
Extended Information