|
【结 构 式】 
|
【分子编号】46383 【品名】3-[5,7-dimethoxy-3-(4-methoxyphenyl)-2-oxo-1(2H)-quinolinyl]propanenitrile 【CA登记号】 |
【 分 子 式 】C21H20N2O4 【 分 子 量 】364.40088 【元素组成】C 69.22% H 5.53% N 7.69% O 17.56% |
合成路线1
该中间体在本合成路线中的序号：(VII)Acylation of 3,5-dimethoxyaniline (I) with 4-methoxyphenylacetyl chloride (II) afforded amide (III). Treatment of (III) with Vilsmeier reagent gave rise to 2-chloroquinoline derivative (IV), which was hydrolyzed to quinolinone (V) using aqueous HOAc. Conjugate addition to (V) of acrylonitrile (VI) produced the cyanoethyl quinolinone (VII). The title tetrazole was then obtained by reaction of nitrile (VII) with tributyltin azide in hot toluene.
| 【1】 Guillaumet, G.; Darro, F.; Frydman, A.; Joseph, B.; Kiss, R. (Laboratoires L. Lafon); Pharmaceutical compsns. comprising 2-quinolones. EP 1097138; FR 2781218; WO 0003990 . |
| 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) | 25780 | 3,5-dimethoxyaniline; 3,5-dimethoxyphenylamine | 10272-07-8 | C8H11NO2 | 详情 | 详情 |
| (II) | 26758 | 2-(4-methoxyphenyl)acetyl chloride | 4693-91-8 | C9H9ClO2 | 详情 | 详情 |
| (III) | 46380 | N-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acetamide | C17H19NO4 | 详情 | 详情 | |
| (IV) | 46381 | 2-chloro-5,7-dimethoxy-3-(4-methoxyphenyl)quinoline; 4-(2-chloro-5,7-dimethoxy-3-quinolinyl)phenyl methyl ether | C18H16ClNO3 | 详情 | 详情 | |
| (V) | 46382 | 5,7-dimethoxy-3-(4-methoxyphenyl)-2(1H)-quinolinone | C18H17NO4 | 详情 | 详情 | |
| (VI) | 10847 | Acrylonitrile | 107-13-1 | C3H3N | 详情 | 详情 |
| (VII) | 46383 | 3-[5,7-dimethoxy-3-(4-methoxyphenyl)-2-oxo-1(2H)-quinolinyl]propanenitrile | C21H20N2O4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)The cyclization of 3,5-dimethoxyaniline (I) with 2-formyl-2-(4-methoxyphenyl)acetic acid ethyl ester (II) by means of polyphosphoric acid trimethylsilyl ester (PPSE) by heating at 110 C gives the quinolone (III), which is alkylated with vinyl cyanide (IV) by means of Triton B in DMF to yield the propionitrile derivative (V). Finally, the cyano group of (V) is converted into the target tetrazolyl derivative by cyclization with tri-tert-butylstannyl azide in refluxing toluene.
| 【1】 Joseph, B.; et al.; 3-Aryl-2-quinolone derivatives: Synthesis and characterization of in vitro and in vivo antitumor effects with emphasis on a new therapeutical target connected with cell migration. J Med Chem 2002, 45, 12, 2543. |
| 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) | 25780 | 3,5-dimethoxyaniline; 3,5-dimethoxyphenylamine | 10272-07-8 | C8H11NO2 | 详情 | 详情 |
| (II) | 48551 | ethyl 2-(4-methoxyphenyl)-3-oxopropanoate | C12H14O4 | 详情 | 详情 | |
| (III) | 46382 | 5,7-dimethoxy-3-(4-methoxyphenyl)-2(1H)-quinolinone | C18H17NO4 | 详情 | 详情 | |
| (IV) | 10847 | Acrylonitrile | 107-13-1 | C3H3N | 详情 | 详情 |
| (V) | 46383 | 3-[5,7-dimethoxy-3-(4-methoxyphenyl)-2-oxo-1(2H)-quinolinyl]propanenitrile | C21H20N2O4 | 详情 | 详情 |