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【结 构 式】 
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【分子编号】11607 【品名】2,1,3-benzoxadiazole 1-oxide; 2,1,3-benzoxadiazol-1-ium-1-olate 【CA登记号】480-96-6 |
【 分 子 式 】C6H4N2O2 【 分 子 量 】136.11004 【元素组成】C 52.95% H 2.96% N 20.58% O 23.51% |
合成路线1
该中间体在本合成路线中的序号：(I)Tirapazamine can be obtained by several related ways: 1) By condensation of benzofurazan (I) with cyanamide disodium salt (II) in hot methanol/water. 2) The condensation of 2-nitroaniline (III) with cyanamide (IV) by heating at 100 C gives 3-amino-1,2,4-bezotriazine 1-oxide (V), which is then oxidized with 30% aqueous H2O2 in hot acetic acid. 3) The reaction of 3-hydroxy-1,2,4-benzotriazine 1-oxide (VI) with refluxing POCl3 and dimethylaniline gives 3-chloro-1,2,4-benzotriazine 1-oxide (VII), which by reaction with dry ammonia in ethanol is converted into the corresponding amino derivative (V), already obtained.
| 【1】 Schofield, K.; Robbins, R.F.; Polyazabicyclic compounds. Part II. Further derivatives of benzo-1:2:4-triazine. J Chem Soc 1957, 3186. |
| 【2】 Tennant, G.; Mason, J.C.; Heterocyclic N-oxides. Part VI. Synthesis and nuclear magnetic resonance spectra of 3-aminobenzo-1,2,4-triazines and their mono- and di-N-oxides. J Chem Soc B 1970, 911. |
| 【3】 Robinson, C.; Castaner, J.; Tirapazamine. Drugs Fut 1995, 20, 3, 256. |
| 【4】 Ley, K.; Seng, F.; Metzer, K.G. (Bayer AG); 3-Amino-1,2,4-benzotriazine-1,4-di-N-oxides and processes for their preparation. US 3868371; US 3980779; US 4001410 . |
| 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) | 11607 | 2,1,3-benzoxadiazole 1-oxide; 2,1,3-benzoxadiazol-1-ium-1-olate | 480-96-6 | C6H4N2O2 | 详情 | 详情 |
| (II) | 63311 | 2-chloro-1-ethoxyethyl ethyl ether; 2-chloro-1,1-diethoxyethane | C6H13ClO2 | 详情 | 详情 | |
| (III) | 11608 | o-Nitroaniline; 2-Nitroaniline; 2-Nitrophenylamine | 88-74-4 | C6H6N2O2 | 详情 | 详情 |
| (IV) | 19648 | Cyanamide | 420-04-2 | CH2N2 | 详情 | 详情 |
| (V) | 11609 | 3-amino-1,2,4-benzotriazin-1-ium-1-olate; 3-Amino-1,2,4-benzotriazine-1-oxide | 5424-06-6 | C7H6N4O | 详情 | 详情 |
| (VI) | 11610 | 3-hydroxy-1,2,4-benzotriazin-1-ium-1-olate | C7H5N3O2 | 详情 | 详情 | |
| (VII) | 11611 | 3-chloro-1,2,4-benzotriazin-1-ium-1-olate | C7H4ClN3O | 详情 | 详情 |