2-(allylamino)pyrido[2,3-d]pyrimidin-4(3H)-one | 35857-96-6

• 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: 2-(allylamino)pyrido[2,3-d]pyrimidin-4(3H)-one
• 英文别名: 2-allylamino-3H-pyrido[2,3-d]pyrimidin-4-one；2-(prop-2-enylamino)-3H-pyrido[2,3-d]pyrimidin-4-one
• CAS: 35857-96-6
• 化学式: C₁₀H₁₀N₄O
• 分子量: 202.216
• InChiKey: WUTGTVMEGNJXSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(allylamino)pyrido[2,3-d]pyrimidin-4(3H)-one 在 碘 、 sodium iodide 、 sodium acetate 作用下， 以 氯仿 、 丙酮 、 甲醇 为溶剂， 反应 57.0h， 以52%的产率得到9-(iodomethyl)-8,9-dihydroimidazo[1,2-a]pyrido-[3,2-e]pyrimidin-5(7H)-one
  参考文献：
  名称：

  Fused pyrimidine systems: XV. Intramolecular electrophilic cyclization of 2-allyl(propargyl, cinnamyl)amino-pyrido[2,3-d]pyrimidin-4(3H)-ones

  摘要：

  2-(Allylamino)- and 2-(propargylamino)pyrido[2,3-d]pyrimidin-4(3H)-ones underwent intramolecular cyclization on heating in polyphosphoric acid to give angularly fused imidazo[1,2-a]pyrido[3,2-e]pyrimidin-5-ones. The cyclization of 2-(cinnamylamino)pyrido[2,3-d]pyrimidin-4(3H)-one under analogous conditions afforded linearly fused 4-phenyl-1,2,3,4-tetrahydro-6H-pyrido[2,3-d]pyrimido[1,2-a]pyrimidin-6-one. 2-(Allylamino)pyrido[2,3-d]pyrimidin-4(3H)-one reacted with iodine yielding 9-(iodomethyl)-8,9-dihydroimidazo[1,2-a]pyrido[3,2-e]pyrimidin-5(7H)-one as the major product, 2-(propargylamino)pyrido[2,3-d]pyrimidin-4(3H)-one gave rise to iodine addition product to the triple bond, and angularly fused 9-iodo-10-phenyl-7,8,9,10-tetrahydro-5H-pyrido[3,2-e]pyrimido[1,2-a]pyrimidin-5-one was obtained from the 2-(cinnamylamino) derivative. Electrophilic cyclization of 2-(allylamino)- and 2-(cinnamylamino)pyrido[2,3-d]pyrimidin-4(3H)-ones by the action of phenylsulfanyl chloride led to the formation of angularly fused 9-(phenylsulfanylmethyl)-8,9-dihydroimidazo[1,2-a]pyrido[3,2-e]pyrimidin-5(7H)-one and 10-phenyl-9-phenylsulfanyl-7,8,9,10-tetrahydro-5H-pyrido[3,2-e]pyrimido[1,2-a]pyrimidin-5-one.

  DOI：

  10.1134/s1070428015040168
• 作为产物：
  描述：

  2-chloropyrido[2,3-d]pyrimidin-4(3H)-one 、 丙烯胺 以 乙醇 为溶剂， 以83%的产率得到2-(allylamino)pyrido[2,3-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Fused pyrimidine systems: XV. Intramolecular electrophilic cyclization of 2-allyl(propargyl, cinnamyl)amino-pyrido[2,3-d]pyrimidin-4(3H)-ones

  摘要：

  2-(Allylamino)- and 2-(propargylamino)pyrido[2,3-d]pyrimidin-4(3H)-ones underwent intramolecular cyclization on heating in polyphosphoric acid to give angularly fused imidazo[1,2-a]pyrido[3,2-e]pyrimidin-5-ones. The cyclization of 2-(cinnamylamino)pyrido[2,3-d]pyrimidin-4(3H)-one under analogous conditions afforded linearly fused 4-phenyl-1,2,3,4-tetrahydro-6H-pyrido[2,3-d]pyrimido[1,2-a]pyrimidin-6-one. 2-(Allylamino)pyrido[2,3-d]pyrimidin-4(3H)-one reacted with iodine yielding 9-(iodomethyl)-8,9-dihydroimidazo[1,2-a]pyrido[3,2-e]pyrimidin-5(7H)-one as the major product, 2-(propargylamino)pyrido[2,3-d]pyrimidin-4(3H)-one gave rise to iodine addition product to the triple bond, and angularly fused 9-iodo-10-phenyl-7,8,9,10-tetrahydro-5H-pyrido[3,2-e]pyrimido[1,2-a]pyrimidin-5-one was obtained from the 2-(cinnamylamino) derivative. Electrophilic cyclization of 2-(allylamino)- and 2-(cinnamylamino)pyrido[2,3-d]pyrimidin-4(3H)-ones by the action of phenylsulfanyl chloride led to the formation of angularly fused 9-(phenylsulfanylmethyl)-8,9-dihydroimidazo[1,2-a]pyrido[3,2-e]pyrimidin-5(7H)-one and 10-phenyl-9-phenylsulfanyl-7,8,9,10-tetrahydro-5H-pyrido[3,2-e]pyrimido[1,2-a]pyrimidin-5-one.

  DOI：

  10.1134/s1070428015040168