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【结 构 式】 
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【分子编号】57751 【品名】10H-Phenothiazine; 2,3,5,6-Dibenzo-1,4-thiazine; Dibenzo-1.4-thiazine; Dibenzothiazine; Phenothiazine; Thiodiphenylamine 【CA登记号】92-84-2 |
【 分 子 式 】C12H9NS 【 分 子 量 】199.2762 【元素组成】C 72.33% H 4.55% N 7.03% S 16.09% |
合成路线1
该中间体在本合成路线中的序号：(IV)4-Chloro-1-butanol (I) is protected as the tetrahydropyranyl ether (III) by treatment with dihydropyran (II) in the presence of pyridinium p-toluenesulfonate (PPTS). Alkylation of the sodium derivative of phenothiazine (IV) with chloride (III) yields adduct (V), which is subsequently deprotected to alcohol (VI) with PPTS in MeOH-THF. The free alcohol (VI) is then chlorinated to (VII) by using SOCl2 in benzene. Finally, condensation of chloride (VII) with pyrrolidine (VIII) in THF at 100 C in a sealed tube provides the title compound.
| 【1】 Guan, J.; et al.; Design, synthesis, and evaluation of new chemosensitizers in multi-drug-resistant Plasmodium falciparum. J Med Chem 2002, 45, 13, 2741. |
| 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) | 22336 | 4-chloro-1-butanol | 928-51-8 | C4H9ClO | 详情 | 详情 |
| (II) | 13684 | 3,4-Dihydro-2H-pyran;2,3-Dihydro-4H-pyran; 5,6-Dihydro-4H-pyran;Dihydropyran | 110-87-2 | C5H8O | 详情 | 详情 |
| (III) | 57750 | 2-(4-Chlorobutoxy)tetrahydropyran | C9H17ClO2 | 详情 | 详情 | |
| (IV) | 57751 | 10H-Phenothiazine; 2,3,5,6-Dibenzo-1,4-thiazine; Dibenzo-1.4-thiazine; Dibenzothiazine; Phenothiazine; Thiodiphenylamine | 92-84-2 | C12H9NS | 详情 | 详情 |
| (V) | 57752 | 4-(10H-phenothiazin-10-yl)butyl tetrahydro-2H-pyran-2-yl ether; 10-[4-(tetrahydro-2H-pyran-2-yloxy)butyl]-10H-phenothiazine | C21H25NO2S | 详情 | 详情 | |
| (VI) | 57753 | 4-(10H-phenothiazin-10-yl)-1-butanol | C16H17NOS | 详情 | 详情 | |
| (VII) | 57754 | 10-(4-chlorobutyl)-10H-phenothiazine | C16H16ClNS | 详情 | 详情 | |
| (VIII) | 11376 | Pyrrolidine | 123-75-1 | C4H9N | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)Alkylation of phenothiazine (I) by ethyl chloroacetate (II) in the presence of K2CO3 affords the ester (III). Subsequent condensation of (III) with thiosemicarbazide (IV) gives the acyl thiosemicarbazide (V), which is cyclized to the thiadiazole derivative (VI) in concentrated H2SO4. Finally, Mannich condensation of aminothiadiazole (VI) with thiobarbituric acid (VII) and formaldehyde furnishes the desired compound.
| 【1】 Archana; Rani, P.; Bajaj, K.; Srivastava, V.K.; Chandra, R.; Kumar, A.; Synthesis of newer indolyl/phenothiazinyl substituted 2-oxo/thiobarbituric acid derivatives as potent anticonvulsant agents. Arzneim-Forsch Drug Res 2003, 53, 5, 301. |
| 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) | 57751 | 10H-Phenothiazine; 2,3,5,6-Dibenzo-1,4-thiazine; Dibenzo-1.4-thiazine; Dibenzothiazine; Phenothiazine; Thiodiphenylamine | 92-84-2 | C12H9NS | 详情 | 详情 |
| (II) | 16601 | ethyl chloroacetate; ethyl 2-chloroacetate | 105-39-5 | C4H7ClO2 | 详情 | 详情 |
| (III) | 64835 | ethyl 2-(10H-phenothiazin-10-yl)acetate | C16H15NO2S | 详情 | 详情 | |
| (IV) | 12954 | 1-Hydrazinecarbothioamide; Thiosemicarbazide | 79-19-6 | CH5N3S | 详情 | 详情 |
| (V) | 64836 | 2-[2-(10H-phenothiazin-10-yl)acetyl]-1-hydrazinecarbothioamide | C15H14N4OS2 | 详情 | 详情 | |
| (VI) | 64837 | 5-(10H-phenothiazin-10-ylmethyl)-1,3,4-thiadiazol-2-amine; 5-(10H-phenothiazin-10-ylmethyl)-1,3,4-thiadiazol-2-ylamine | C15H12N4S2 | 详情 | 详情 | |
| (VII) | 64838 | 2-thioxodihydro-4,6(1H,5H)-pyrimidinedione | C4H4N2O2S | 详情 | 详情 |