【结 构 式】 |
【分子编号】31476 【品名】4,6,7,8-tetrahydro-2,5(1H,3H)-quinolinedione 【CA登记号】 |
【 分 子 式 】C9H11NO2 【 分 子 量 】165.19188 【元素组成】C 65.44% H 6.71% N 8.48% O 19.37% |
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)The reaction of cyclohexane-1,3-dione (I) with ammonia gives 3-amino-2-cyclohexen-1-one (II), which is cyclized with acrylic acid (III) by heating at 140 C yielding 1,2,3,4,5,6,7,8-octahydroquinoline-2,5-dione (IV). The dehydrogenation of (IV) by means of Pd/C in refluxing decaline affords 5-hydroxy-1,2,3,4-tetrahydroquinolin-2-one (V), which is condensed with epichlorohydrin (VI) by means of NaOMe or NaOH in methanol giving 5-(2,3-epoxypropoxy)-1,2,3,4-tetrahydroquinolin-2-one (VII). Finally, this compound is treated with tert-butylamine in methanol.
【1】 Castaner, J.; Sungurbey, K.; Carteolol. Drugs Fut 1977, 2, 5, 288. |
【2】 Shono, T.; et al.; A new practical synthesis of 5-hydroxy-3,4-dihydrocarbostyril and 5-hydroxycarbostyril. J Org Chem 1981, 46, 3719. |
【3】 Von Winkler, W.; Chemical and analytical data for the pharmaceutically active substance carteolol hydrochloride. Arzneim-Forsch Drug Res 1983, 33, 2a, 279. |
【4】 Mori, H.; Tamura, Y,.; Tominaga, M.; Yoshiaki, S.; Nakagawa, K.; Murakami, N. (Otsuka Pharmaceutical Co., Ltd.); 3,4-Dihydrocarbostyril derivs., their preparation, and pharmaceutical compsns. thereof. DE 2302027; GB 1424571 . |
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) | 11244 | 1,3-Cyclohexanedione | 504-02-9 | C6H8O2 | 详情 | 详情 |
(II) | 31475 | 3-amino-2-cyclohexen-1-one | 5220-49-5 | C6H9NO | 详情 | 详情 |
(III) | 19139 | acrylic acid | 79-10-7 | C3H4O2 | 详情 | 详情 |
(IV) | 31476 | 4,6,7,8-tetrahydro-2,5(1H,3H)-quinolinedione | C9H11NO2 | 详情 | 详情 | |
(V) | 31477 | 5-hydroxy-3,4-dihydro-2(1H)-quinolinone | C9H9NO2 | 详情 | 详情 | |
(VI) | 29648 | 2-oxiranylmethanol | 556-52-5 | C3H6O2 | 详情 | 详情 |
(VII) | 31478 | 5-(2-oxiranylmethoxy)-3,4-dihydro-2(1H)-quinolinone | C12H13NO3 | 详情 | 详情 | |
(VIII) | 17895 | 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine | 75-64-9 | C4H11N | 详情 | 详情 |
Extended Information