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【结 构 式】

【分子编号】46767

【品名】2-amino-1-(1H-indol-3-yl)-1-ethanone

【CA登记号】

【 分 子 式 】C10H10N2O

【 分 子 量 】174.20228

【元素组成】C 68.95% H 5.79% N 16.08% O 9.18%

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:(V)

Reaction of indole (I) with chloroacetyl chloride (II) in the presence of pyridine in toluene afforded the chloro ketone (III). This was then treated with sodium azide in aqueous acetone to furnish the azido ketone (IV). Hydrogenation of (IV) over Pd/C in the presence of HCl gave the amino ketone (V). The intermediate 3-indolylglyoxylic chloride (VI) was obtained by acylation of indole (I) with oxalyl chloride in CH2Cl2. Subsequent condensation between acid chloride (VI) and amino ketone (V) produced amide (VII). This was finally cyclized to the desired bisindolyl pyrazinone by treatment with ammonia in a pressure vessel.

1 Jiang, B.; Gu, X.-H.; Syntheses and cytotoxicity evaluation of bis(indolyl)thiazole, bis(indolyl)pyrazinone and bis(indolyl)pyrazine: Analogues of cytotoxic marine bis(indole) alkaloid. Bioorg Med Chem 2000, 8, 2, 363.
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) 15292 Indole; 1H-indole 120-72-9 C8H7N 详情 详情
(II) 11296 2-Chloroacetyl chloride; Chloroacetic chloride 79-04-9 C2H2Cl2O 详情 详情
(III) 46764 2-chloro-1-(1H-indol-3-yl)-1-ethanone C10H8ClNO 详情 详情
(IV) 46765 2-azido-1-(1H-indol-3-yl)-1-ethanone C10H8N4O 详情 详情
(V) 46767 2-amino-1-(1H-indol-3-yl)-1-ethanone C10H10N2O 详情 详情
(VI) 13476 Indole-3-glyoxylyl chloride; 2-(1H-Indol-3-yl)-2-oxoacetyl chloride 22980-09-2 C10H6ClNO2 详情 详情
(VII) 46768 2-(1H-indol-3-yl)-N-[2-(1H-indol-3-yl)-2-oxoethyl]-2-oxoacetamide C20H15N3O3 详情 详情
Extended Information