3-<(Benzyloxycarbonyl)amino>-4H-pyrimido<1,2-b>pyridazin-4-one | 225112-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-<(Benzyloxycarbonyl)amino>-4H-pyrimido<1,2-b>pyridazin-4-one
• 英文别名: 3-[(benzyloxycarbonyl)amino]-4H-pyrimido[1,2-b]pyridazin-4-one；3-(benzyloxycarbonyl)amino-4H-pyrimido[1,2-b]pyridazin-4-one；benzyl N-(4-oxopyrimido[1,2-b]pyridazin-3-yl)carbamate
• CAS: 225112-17-4
• 化学式: C₁₅H₁₂N₄O₃
• 分子量: 296.285
• InChiKey: PGLZZCWDMOMMSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-<(Benzyloxycarbonyl)amino>-4H-pyrimido<1,2-b>pyridazin-4-one 在 氢溴酸 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 3-[N-α-(D)-mannopyranosyl]amino-4H-pyrimido[1,2-b]pyridazin-4-one
  参考文献：
  名称：

  Synthesis and Characterisation of Some New N-Glycosides Containing Substituted Pyridopyrimidinone, Pyrimidopyridazinone, Thiazolopyrimidinone and Quinolizin-4-one Moiety

  摘要：

  A series of new N-glycosides (D-glucosides, D-mannosides, L- and D-arabinosides, D-Xylosides and one D-galactoside) containing heterocyclic moiety have been prepared by reaction of the corresponding heterocyclic amines with pyranoses in boiling methanol. The structures of the prepared compounds have been studied by means of proton and carbon NMR spectroscopy. In the most cases the products existed in DMSO solution as the single anomers.

  DOI：

  10.3987/com-08-11414
• 作为产物：
  描述：

  CBZ-甘氨酸甲酯 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 3-<(Benzyloxycarbonyl)amino>-4H-pyrimido<1,2-b>pyridazin-4-one
  参考文献：
  名称：

  Synthesis and Characterisation of Some New N-Glycosides Containing Substituted Pyridopyrimidinone, Pyrimidopyridazinone, Thiazolopyrimidinone and Quinolizin-4-one Moiety

  摘要：

  A series of new N-glycosides (D-glucosides, D-mannosides, L- and D-arabinosides, D-Xylosides and one D-galactoside) containing heterocyclic moiety have been prepared by reaction of the corresponding heterocyclic amines with pyranoses in boiling methanol. The structures of the prepared compounds have been studied by means of proton and carbon NMR spectroscopy. In the most cases the products existed in DMSO solution as the single anomers.

  DOI：

  10.3987/com-08-11414

文献信息

• Methyl (Z)-2-[(Benzyloxycarbonyl)amino]-3-dimethyl- aminopropenoate in the Synthesis of Heterocyclic Systems. Synthesis of (Benzyloxycarbonyl)amino Substituted Fused Pyrimidinones
  作者：Renata Toplak、Jurij Svete、Simona Golič Grdadolnik、Branko Stanovnik

  DOI：10.1135/cccc19990177

  日期：——

  Methyl (Z)-2-[(benzyloxycarbonyl)amino]-3-dimethylaminopropenoate (1) was used as a reagent for preparation of 3-[(benzyloxycarbonyl)amino] substituted 4H-pyrido[1,2-a]pyrimidin-4-ones 17-21, 4H-pyrimido[1,2-b]pyridazin-4-ones 22 and 23, 5H-[1,2,4]triazolo[2,3-a]- pyrimidin-5-one 24, 5H-thiazolo[3,2-a]pyrimidin-5-one 25, and 4H-pyrazino[1,2-a]pyrimidin-4-one 26. Removal of the benzyloxycarbonyl group by catalytical transfer hydrogenation with Pd/C in the presence of cyclohexene is selective to give 3-amino-4H-pyrido[1,2-a]- pyrimidin-4-ones 27-30 in 85-92% yields, or with hydrogen bromide in acetic acid to give 3-amino-4H-pyrimido[1,2-b]pyridazin-4-one (31) and 6-amino-5H-thiazolo[3,2-a]pyrimidin-5-one (32) in 80% yields.

  甲基（Z）-2-[(苄氧羰基)氨基]-3-二甲基氨基丙烯酸酯（1）被用作3-[(苄氧羰基)氨基]取代的4H-吡啶并[1,2-a]嘧啶-4-酮17-21，4H-嘧啶并[1,2-b]吡啉并[1,2-b]吡啉-4-酮22和23，5H-[1,2,4]三唑并[2,3-a]嘧啶-5-酮24，5H-噻唑并[3,2-a]嘧啶-5-酮25和4H-吡嗪并[1,2-a]嘧啶-4-酮26的制备试剂。在Pd/C存在下和环己烯的存在下，通过催化转移氢化去除苄氧羰基团是选择性的，可以得到85-92%产率的3-氨基-4H-吡啶并[1,2-a]嘧啶-4-酮27-30，或者通过在乙酸中使用溴化氢得到3-氨基-4H-嘧啶并[1,2-b]吡啉并[1,2-b]吡啉-4-酮（31）和6-氨基-5H-噻唑并[3,2-a]嘧啶-5-酮（32）80%的产率。
• Catalytic hydrogenation of 3-benzyloxycarbonylaminoazino[1,2-<i>x</i>]-azin-4-ones. A facile access to 3-amino-6,7,8,9-tetrahydro-4<i>H</i>-pyrido[1,2-<i>a</i>]pyridin-4-ones and 3-Amino-6,7,8,9-tetrahydro-4<i>H</i>-azino[1,2-<i>x</i>]pyrimidin-4-ones
  作者：Simon Rečnik、Renata Toplak、Jurij Svete、Lucija Pizzioli、Branko Stanovnik

  DOI：10.1002/jhet.5570370420

  日期：2000.7

  By catalytic hydrogenation of 3-(benzyloxycarbonyl)amino-4H-pyrido[1,2-a]pyridin-4-ones 28 and 29, and azino[1,2-x]pyrimidin-4-ones 32–35, 41, and 42, partial saturation of the heterocyclic systems and removal of the benzyloxycarbonyl moiety was observed to give 3-amino-6,7,8,9-tetrahydro-4H-pyrido[1,2 a]pyridin-4-ones 30 and 31, and 3-amino-6,7,8,9-tetrahydro-4H-azino[1,2-x]pyrimidin-4-ones 36–39

  通过催化氢化3-（苄氧羰基）氨基-4 H-吡啶并[1,2- a ]吡啶-4-酮28和29，以及叠氮基[1,2 - x ]嘧啶-4-酮32-35，41，和42时，观察到杂环体系和除去苄氧羰基结构部分中的部分饱和，得到3-氨基-6,7,8,9-四氢-4- ħ -吡啶并[1,2一]吡啶-4-酮30和31和3-氨基-6,7,8,9-四氢-4 H-叠氮[1,2 - x ]嘧啶-4-酮36-39、43和44高产。该方法代表简单的两步合成，从杂环α-氨基化合物和（Z）-2-（苄氧基羰基）氨基-3-二甲基氨基丙酸甲酯开始，然后进行催化氢化。