【结 构 式】 |
【分子编号】40687 【品名】7-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione 【CA登记号】 |
【 分 子 式 】C10H8INO2 【 分 子 量 】301.08353 【元素组成】C 39.89% H 2.68% I 42.15% N 4.65% O 10.63% |
合成路线1
该中间体在本合成路线中的序号:(VI)5-Iodoanthranilic acid (I) was converted to ethyl ester (II) (1), which was subsequently reacted with ethoxysuccinyl chloride (III) to furnish the amide (IV). Dieckmann cyclization of (IV) using KH produced ketoester (V), and further dealkoxycarbonylation by heating in wet DMSO gave rise to benzazepinedione (VI). After formation of the corresponding hydrazone (VIII) with 4-(trifluoromethyl)phenylhydrazine (VII), Fisher indole synthesis yielded the paulone system (IX). The Heck reaction of (IX) with acrylonitrile in the presence of palladium catalyst gave adduct (X). The target saturated analogue was finally prepared by refluxing the acrylonitrile derivative (X) with Mg in MeOH.
【1】 Kunick, C.; Jalluri, R.K.; Sausville, E.A.; Gussio, R.; Zaharevitz, D.W.; Meijer, L.; Lemdke, T.; schultz, C.; Leost, M.; 2-Substituted paullones: CDK1/cyclin B-inhibiting property and in vitro antiproliferative activity. Bioorg Med Chem Lett 2000, 10, 6, 567. |
【2】 Gussio, R.; Zaharevitz, D.W.; Sausville, E.A.; Jalluri, R.K. (US Department of Health & Human Services); Fused azepinone cyclin dependent kinase inhibitors. WO 9965910 . |
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) | 19964 | 5-Iodoanthranilic acid; 2-amino-5-iodobenzoic acid | 5326-47-6 | C7H6INO2 | 详情 | 详情 |
(II) | 40683 | ethyl 2-amino-5-iodobenzoate | C9H10INO2 | 详情 | 详情 | |
(III) | 40684 | ethyl 4-chloro-4-oxobutanoate; Ethyl succinyl chloride | 14794-31-1 | C6H9ClO3 | 详情 | 详情 |
(IV) | 40685 | ethyl 2-[(4-ethoxy-4-oxobutanoyl)amino]-5-iodobenzoate | C15H18INO5 | 详情 | 详情 | |
(V) | 40686 | ethyl 5-hydroxy-7-iodo-2-oxo-2,3-dihydro-1H-1-benzazepine-4-carboxylate | C13H12INO4 | 详情 | 详情 | |
(VI) | 40687 | 7-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione | C10H8INO2 | 详情 | 详情 | |
(VII) | 40688 | 1-[4-(trifluoromethyl)phenyl]hydrazine | 368-90-1 | C7H7F3N2 | 详情 | 详情 |
(VIII) | 40689 | 7-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione 5-[N-[4-(trifluoromethyl)phenyl]hydrazone] | C17H13F3IN3O | 详情 | 详情 | |
(IX) | 40690 | 2-iodo-9-(trifluoromethyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one | C17H10F3IN2O | 详情 | 详情 | |
(X) | 40691 | (E)-3-[6-oxo-9-(trifluoromethyl)-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepin-2-yl]-2-propenenitrile | C20H12F3N3O | 详情 | 详情 |