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【结 构 式】 
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【分子编号】48113 【品名】4-hydrazinopyrrolo[1,2-a]quinoxaline 【CA登记号】 |
【 分 子 式 】C11H10N4 【 分 子 量 】198.22736 【元素组成】C 66.65% H 5.08% N 28.26% |
合成路线1
该中间体在本合成路线中的序号：(VI)Clauson-Kaas reaction between 2-fluoroaniline (I) and 2,5-dimethoxytetrahydrofuran (II) in refluxing HOAc affords pyrrolic compound (III), which is then converted into cyanopyrrole derivative (IV) through a one-pot sequence involving formylation with oxalyl chloride, oximation with NH2OH.HCl and dehydration with Ac2O. Cyclization of nitrile (IV) by treatment with KOH in ethylene glycol or in tert-butyl alcohol yields quinoxalinone derivative (V), which is then transformed into the hydrazine derivative (VI) by refluxing with POCl3 and catalytic N,N-dimethylaniline followed by treatment with hydrazine in MeOH. Finally, the desired product is obtained by reaction of (VI) with pyrazinecarboxylic acid (VII) in the presence of PPh3 and 2,2'-dipyridyl disulfide (Aldrithiol-2) in CH2Cl2.
| 【2】 Campiani, G.; et al.; Novel and highly potent 5-HT3 receptor agonists based on a pyrroloquinoxaline structure. J Med Chem 1997, 40, 22, 3670. |
| 【1】 Campiani, G.; Fabbrini, M.; Aiello, F.; et al.; Quinoxalinylethylpyridylthioureas (QXPTs) as potent non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors. Further SAR studies and identification of a novel orally bioavailable hydrazine-based antiviral agent. J Med Chem 2001, 44, 3, 305. |
| 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) | 22296 | 2-fluorophenylamine; 2-fluoroaniline | 348-54-9 | C6H6FN | 详情 | 详情 |
| (II) | 12132 | 2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether | 696-59-3 | C6H12O3 | 详情 | 详情 |
| (III) | 48110 | 1-(2-fluorophenyl)-1H-pyrrole | C10H8FN | 详情 | 详情 | |
| (IV) | 48111 | 1-(2-fluorophenyl)-1H-pyrrole-2-carbonitrile | C11H7FN2 | 详情 | 详情 | |
| (V) | 48112 | pyrrolo[1,2-a]quinoxalin-4(5H)-one | C11H8N2O | 详情 | 详情 | |
| (VI) | 48113 | 4-hydrazinopyrrolo[1,2-a]quinoxaline | C11H10N4 | 详情 | 详情 | |
| (VII) | 37256 | 2-pyrazinecarboxylic acid; Pyrazinoic acid | 98-97-5 | C5H4N2O2 | 详情 | 详情 |