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【结 构 式】 
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【分子编号】51719 【品名】5-[(E)-(6-hydroxy-2-naphthyl)methylidene]-1,3-thiazolidine-2,4-dione 【CA登记号】 |
【 分 子 式 】C14H9NO3S 【 分 子 量 】271.2964 【元素组成】C 61.98% H 3.34% N 5.16% O 17.69% S 11.82% |
合成路线1
该中间体在本合成路线中的序号：(V)Reduction of 6-hydroxynaphthalen-2-carboxylic acid (I) by means of trimethyl borate and BH3.THF complex obtained by reaction of NaBH4 and dimethyl sulfate in THF yields the naphthyl carbinol derivative (II), which is oxidized to aldehyde (III) with either manganese dioxide in DMF or acetone, mixtures of CuCl2, CuBr2 or FeCl3 with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) in DMF or O2, TEMPO and a ruthenium catalyst in chlorobenzene. Condensation of aldehyde (III) with thiazolidine-2,4-dione (IV) in 2-methoxyethanol, 2-propanol, DMF or DMSO gives 5-(6-hydroxynaphthalen-2-ylmethylene)thiazolidine-2,4-dione (V), which is then reduced with either H2 over catalyst or cyclohexene to provide 5-(6-hydroxynaphthalen-2-ylmethyl)thiazolidine-2,4-dione (VI). Finally, compound (VI) is condensed with 2-fluorobenzyl chloride (VII) by means of NaH or KH in DMF, DMSO or NMP.
| 【1】 del Fresno, M.; Sorbera, L.A.; Castaner, J.; Silvestre, J.S.; Netoglitazone. Drugs Fut 2002, 27, 2, 132. |
| 【2】 Ohe, T.; Suehiro, I.; Sekiya, T.; Ueno, H. (Mitsubishi Chemical Corp.); Preparation method of naphthalene derivs.. JP 1998139768 . |
| 【3】 Ichikawa, S.; Iwane, H.; Qu, J. (Mitsubishi Chemical Corp.); 6-Hydroxy-2-naphthylcarbinol and process for the preparation thereof. WO 0073252 . |
| 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) | 51716 | 6-Hydroxy-2-naphthoic acid; 2-Naphthol-6-carboxylic Acid | 16712-64-4 | C11H8O3 | 详情 | 详情 |
| (II) | 51717 | 6-(hydroxymethyl)-2-naphthol | C11H10O2 | 详情 | 详情 | |
| (III) | 51718 | 6-hydroxy-2-naphthaldehyde | C11H8O2 | 详情 | 详情 | |
| (IV) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
| (V) | 51719 | 5-[(E)-(6-hydroxy-2-naphthyl)methylidene]-1,3-thiazolidine-2,4-dione | C14H9NO3S | 详情 | 详情 | |
| (VI) | 51720 | 5-[(6-hydroxy-2-naphthyl)methyl]-1,3-thiazolidine-2,4-dione | C14H11NO3S | 详情 | 详情 | |
| (VII) | 51721 | alpha-Chloro-2-fluorotoluene; 2-Fluorobenzyl chloride; alpha-Chloro-O-Fluorotoluene; o-Fluorobenzyl chloride; 1-Chloromethyl-2-fluorobenzene | 345-35-7 | C7H6ClF | 详情 | 详情 |