ethyI 6-hydroxy-2-[(hydroxyamino)methyleneamino]-5-oxo-5,6-dihydropyrido[4,3-d]pyrimidine-8-carboxylate | 1142934-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: ethyI 6-hydroxy-2-[(hydroxyamino)methyleneamino]-5-oxo-5,6-dihydropyrido[4,3-d]pyrimidine-8-carboxylate
• 英文别名: Ethyl 6-hydroxy-2-[(hydroxyamino)methylideneamino]-5-oxopyrido[4,3-d]pyrimidine-8-carboxylate；ethyl 6-hydroxy-2-[(hydroxyamino)methylideneamino]-5-oxopyrido[4,3-d]pyrimidine-8-carboxylate
• CAS: 1142934-85-7
• 化学式: C₁₁H₁₁N₅O₅
• 分子量: 293.239
• InChiKey: JSZBSMCPJHMNFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  ethyl 4-[1-(dimethylamino)-3-ethoxy-3-oxoprop-l-en-2-yl]-2-[(dimethylamino)methyleneamino]pyrimidine-5-carboxylate 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以93%的产率得到ethyI 6-hydroxy-2-[(hydroxyamino)methyleneamino]-5-oxo-5,6-dihydropyrido[4,3-d]pyrimidine-8-carboxylate
  参考文献：
  名称：

  Transformations of Diethyl 2-[(Dimethylamino)methylene]-3-oxopentanedioate. A Simple Synthesis of Substituted 2-Amino-5-oxo-5,6-dihydropyrido[4,3-d]pyrimidine-8-carboxylates

  摘要：

  Diethyl 2-[(dimethylamino)methylene]-3-oxopentanedioate (2), prepared from acetone-1,3-dicarboxylates (1) and N,N-dimethylformamide dimethyl acetal (DMFDMA) was, without isolation, transformed by treatment with guanidine hydrochloride into ethyl 2-amino-4-(2-ethoxycarbonylmethyl)-pyrimidine-5-carboxylate (3). Compound 3 was transformed with DMFDMA first into intermediate 4 and with an excess of DMFDMA into ethyl 4-[1-(dimethylamino)-3-ethoxy-3-oxoprop-1-en-2-yl]-2-[(dimethylamino)methyle neamino]pyrimidine-5-carboxylate (5). By treatment of compound 5 with ammonia, primary amines, hydrazine or hydroxylamine intermediates 6a-j were formed, which cyclized into 6-substituted 2-amino-5-oxo-5,6-dihydropyrido[4,3-d]pyridine-8-carboxylates (7a-j).

  DOI：

  10.3987/com-08-s(f)90

文献信息

• Transformations of Diethyl 2-[(Dimethylamino)methylene]-3-oxopentanedioate. A Simple Synthesis of Substituted 2-Amino-5-oxo-5,6-dihydropyrido[4,3-d]pyrimidine-8-carboxylates
  作者：Branko Stanovnik、Silvo Zupančič、Jurij Svete

  DOI：10.3987/com-08-s(f)90

  日期：——

  Diethyl 2-[(dimethylamino)methylene]-3-oxopentanedioate (2), prepared from acetone-1,3-dicarboxylates (1) and N,N-dimethylformamide dimethyl acetal (DMFDMA) was, without isolation, transformed by treatment with guanidine hydrochloride into ethyl 2-amino-4-(2-ethoxycarbonylmethyl)-pyrimidine-5-carboxylate (3). Compound 3 was transformed with DMFDMA first into intermediate 4 and with an excess of DMFDMA into ethyl 4-[1-(dimethylamino)-3-ethoxy-3-oxoprop-1-en-2-yl]-2-[(dimethylamino)methyle neamino]pyrimidine-5-carboxylate (5). By treatment of compound 5 with ammonia, primary amines, hydrazine or hydroxylamine intermediates 6a-j were formed, which cyclized into 6-substituted 2-amino-5-oxo-5,6-dihydropyrido[4,3-d]pyridine-8-carboxylates (7a-j).