4-methyl-7-sulfanyl-2H-pyrano[2,3-b]pyridin-2-one -Drug Synthesis Database

【结构式】

【分子编号】58434

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

【CA登记号】

【分子式】C₉H₇NO₂S

【分子量】193.22612

【元素组成】C 55.94% H 3.65% N 7.25% O 16.56% S 16.6%

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：(IV)

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.

参考文献中间体

合成目标

【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