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【结 构 式】 
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【分子编号】31489 【品名】(E)-3-phenyl-N-[2-(1H-pyrrol-1-yl)phenyl]-2-propenamide 【CA登记号】 |
【 分 子 式 】C19H16N2O 【 分 子 量 】288.34892 【元素组成】C 79.14% H 5.59% N 9.72% O 5.55% |
合成路线1
该中间体在本合成路线中的序号：(VI)The N-arylpyrrole (III) was prepared by the Clauson-Kaas reaction of 2-nitroaniline (I) with 2,5-dimethoxytetrahydrofuran (II) in AcOH under microwave irradiation. Subsequent reduction of the nitro group of (III) using BiCl3 and NaBH4 provided aniline (IV), which was condensed with cinnamoyl chloride (V) in the presence of pyridine to give the corresponding amide (VI). Cyclization of (VI) using POCl3 and pyridine produced the pyrroloquinoxaline (VII), and further Vilsmeier-Haack formylation gave aldehyde (VIII). This was condensed with boiling 3-(dimethylamino)propylamine (IX), and the resulting imine (X) was finally reduced to the target amine with NaBH4 in MeOH. The title compound was finally converted to the trioxalate salt upon treatment with oxalic acid in isopropanol.
| 【1】 Guillon, J.; Rault, S.; Kervran, A.; Renard, P.; Manechez, D.; Pfeiffer, B.; Dallemagne, P.; Synthesis of new pyrrolo[1,2-a]quinoxalines: Potential non-peptide glucagon receptor antagonists. Eur J Med Chem 1998, 33, 4, 293. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 15713 | Oxalic acid | 144-62-7 | C2H2O4 | 详情 | 详情 | |
| (I) | 11608 | o-Nitroaniline; 2-Nitroaniline; 2-Nitrophenylamine | 88-74-4 | C6H6N2O2 | 详情 | 详情 |
| (II) | 12132 | 2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether | 696-59-3 | C6H12O3 | 详情 | 详情 |
| (III) | 31487 | 1-(2-nitrophenyl)-1H-pyrrole | 33265-60-0 | C10H8N2O2 | 详情 | 详情 |
| (IV) | 31488 | 2-(1H-pyrrol-1-yl)aniline; 2-(1H-pyrrol-1-yl)phenylamine | 6025-60-1 | C10H10N2 | 详情 | 详情 |
| (V) | 11303 | (E)-3-Phenyl-2-propenoyl chloride; 3-Phenyl-2-propenoyl chloride | 102-92-1 | C9H7ClO | 详情 | 详情 |
| (VI) | 31489 | (E)-3-phenyl-N-[2-(1H-pyrrol-1-yl)phenyl]-2-propenamide | C19H16N2O | 详情 | 详情 | |
| (VII) | 31490 | 4-[(E)-2-phenylethenyl]pyrrolo[1,2-a]quinoxaline | C19H14N2 | 详情 | 详情 | |
| (VIII) | 31491 | 4-[(E)-2-phenylethenyl]pyrrolo[1,2-a]quinoxaline-1-carbaldehyde | C20H14N2O | 详情 | 详情 | |
| (IX) | 25248 | N-(3-aminopropyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,3-propanediamine | 109-55-7 | C5H14N2 | 详情 | 详情 |
| (X) | 31492 | N-[3-(dimethylamino)propyl]-N-((E)-[4-[(E)-2-phenylethenyl]pyrrolo[1,2-a]quinoxalin-1-yl]methylidene)amine; N(1),N(1)-dimethyl-N(3)-((E)-[4-[(E)-2-phenylethenyl]pyrrolo[1,2-a]quinoxalin-1-yl]methylidene)-1,3-propanediamine | C25H26N4 | 详情 | 详情 |