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【结 构 式】 
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【分子编号】51396 【品名】1-(2-Furyl)methylamine; 2-Aminomethylfuran; 2-Furfurylamine; Furfurylamine 【CA登记号】617-89-0 |
【 分 子 式 】C5H7NO 【 分 子 量 】97.11672 【元素组成】C 61.84% H 7.27% N 14.42% O 16.47% |
合成路线1
该中间体在本合成路线中的序号：(XXI)Benzoylation of furfurylamine (XXI) under Schotten-Baumann conditions provided amide (XXII). The dimethoxy dihydrofuran derivative (XXIII) was then obtained as different diastereomeric mixtures by either the electrolysis of N-benzoylfurfurylamine (XXII) in the presence of NH4Cl in MeOH or by the bromination of (XXII) in MeOH. Oxidative cleavage of (XXIII) using the Jones reagent led to 5-benzamido-4-oxo-2-pentenoic acid (XXIV), which was further hydrogenated to the pentanoic analogue (XXV). Alternatively, (XXV) was also obtained by first hydrogenation of (XXIII) to the tetrahydrofuran (XXVI), which was then subjected to Jones oxidation. Finally, acidic hydrolysis of delta-benzamido levulinic acid (XXV) provided the title compound.
| 【1】 Raphael, R.A.; Marei, A.A.; The synthesis of amino-acids from furfurylamine. J Chem Soc 1958, 2624. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXI) | 51396 | 1-(2-Furyl)methylamine; 2-Aminomethylfuran; 2-Furfurylamine; Furfurylamine | 617-89-0 | C5H7NO | 详情 | 详情 |
| (XXII) | 59153 | N-Furan-2-ylmethylbenzamide | C12H11NO2 | 详情 | 详情 | |
| (XXIII) | 59154 | N-(2,5-Dimethoxy-2,5-dihydrofuran-2-ylmethyl)benzamide | C14H17NO4 | 详情 | 详情 | |
| (XXIV) | 59155 | (E)-5-(benzoylamino)-4-oxo-2-pentenoic acid | C12H11NO4 | 详情 | 详情 | |
| (XXV) | 59156 | 5-(benzoylamino)-4-oxopentanoic acid | C12H13NO4 | 详情 | 详情 | |
| (XXVI) | 59157 | N-[(2,5-dimethoxytetrahydro-2-furanyl)methyl]benzamide | C14H19NO4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)Reaction of 2-aminothiazole (I) with thiocarbonyldiimidazole (II) in acetonitrile gave the intermediate thioimidazolide (III). This was then condensed with 2-furylmethylamine (IV) in hot DMF to yield the title thiourea derivative.
| 【1】 Venkatachalam, T.K.; Sudbeck, E.A.; Mao, C.; Uckun, F.M.; Anti-HIV activity of aromatic and heterocyclic thiazolyl thiourea compounds. Bioorg Med Chem Lett 2001, 11, 4, 523. |
| 【2】 Uckun, F.M.; Venkatachalam, T.K. (Parker Hughes Institute); Aromatic and heterocyclic thiazolyl thiourea cpds. and use. WO 0232889 . |
| 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) | 19795 | 2-Thiazolamine; 1,3-thiazol-2-amine; 1,3-thiazol-2-ylamine | 96-50-4 | C3H4N2S | 详情 | 详情 |
| (II) | 11990 | Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldiimidazole | 6160-65-2 | C7H6N4S | 详情 | 详情 |
| (III) | 51395 | N-(1,3-thiazol-2-yl)-1H-imidazole-1-carbothioamide | C7H6N4S2 | 详情 | 详情 | |
| (IV) | 51396 | 1-(2-Furyl)methylamine; 2-Aminomethylfuran; 2-Furfurylamine; Furfurylamine | 617-89-0 | C5H7NO | 详情 | 详情 |