ethyl 3-[4-(furan-2-ylmethylamino)-4-oxobutanoylamino]-4-oxo-3,4-dihydroquinazoline-2-carboxylate | 1073343-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: ethyl 3-[4-(furan-2-ylmethylamino)-4-oxobutanoylamino]-4-oxo-3,4-dihydroquinazoline-2-carboxylate
• CAS: 1073343-77-7
• 化学式: C₂₀H₂₀N₄O₆
• 分子量: 412.402
• InChiKey: ZEMDBSPHESYMIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  132.53
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2-呋喃甲胺 、 ethyl 3-(2,5-dioxopyrrolidin-1-yl)-4-oxo-3,4-dihydroquinazoline-2-carboxylate 以 1,4-二氧六环 为溶剂， 以82%的产率得到ethyl 3-[4-(furan-2-ylmethylamino)-4-oxobutanoylamino]-4-oxo-3,4-dihydroquinazoline-2-carboxylate
  参考文献：
  名称：

  Synthesis of 3-amino-3,4-dihydroquinazolin-4-one derivatives from anthranilic acid hydrazide and dicarboxylic acids

  摘要：

  Treatment of anthranilic acid hydrazide with 2 equiv of ethoxalyl chloride gave the corresponding diester which underwent cyclization in acetic anhydride to produce ethyl 3-(ethoxalylamino)-4-oxo-3,4-dihydroquinazoline-2-carboxylate. Acylation of anthranilic acid hydrazide first with succinic anhydride and then with ethoxalyl chloride led to the formation of 4-[2-(2-{[ethoxy(oxo)acetyl]amino) benzoyl)hydrazino]-4-oxobutanoic acid whose cyclization in acetic acid afforded N-(2-ethoxycarbonyl-4-oxo-3,4-dihydroquinazolin-3-yl)succinamic acid, while in acetic anhydride ethyl 3-(2,5-dioxopyrrolidin-1-yl)-4-oxo-3,4-dihydroquinazoline-2-carboxylate was obtained. The latter was brought into reactions with amines and hydrazine hydrate and alkaline hydrolysis. Acylation of 2-[2-(2-aminobenzoyl)hydrazinocarbonyl]benzoic acid with ethoxalyl chloride gave ethyl N-[2-(phthalimidocarbamoyl)phenyl]oxamate, and with succinic anhydride, 3-[4-oxo-3-phthalimido-3,4-dihydroquinazolin-2-yl]propionic acid. 4-[2-(2-Aminobenzoyl)hydrazino]-4-oxobutanoic acid reacted with phthalic anhydride in boiling acetic acid to give phthalazino[1,2-b]quinazoline-5,8-dione via elimination of succinic acid residue.

  DOI：

  10.1134/s1070428007120160