5-imino-7-phenyl-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carbonitrile | 136498-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-imino-7-phenyl-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carbonitrile
• 英文别名: 5-Imino-7-phenyl-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidine-6-carbonitrile
• CAS: 136498-25-4
• 化学式: C₁₃H₁₀N₄S
• 分子量: 254.315
• InChiKey: UVXITFPKVPMBJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  88.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-imino-7-phenyl-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carbonitrile 在 硫酸 作用下， 反应 2.0h， 以13%的产率得到5-Oxo-7-phenyl-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
  参考文献：
  名称：

  碳酸碳酸亚铵盐。XI †。由N-保护的2-甲硫基-1,3-噻嗪鎓盐和2-甲硫基噻唑鎓盐合成含N，S的杂环。第3部分。N保护的2-甲硫基-1,3-噻嗪鎓盐和2-甲硫基噻唑鎓盐与3-氨基-2-氰基-3-芳基丙烯腈的反应‡

  摘要：

  Ñ -Boc保护的2- memylthio -1,3-噻嗪1和2-methylthiothiazolium碘化物2,3从相应的3,4,5,6-四氢-2-获得ħ -1,3-噻嗪-2-硫酮和噻唑烷-2-硫酮在甲基碘的作用下与3-armno-2-cyano-3-芳基丙烯腈反应形成环状异硫脲5-7。用三氟乙酸除去保护基，然后将所需的环化成3,4-二氢-2 H，6 H-嘧啶基[ 2,1- b ] [1,3]噻嗪8a-c，8a'-c'和噻唑罗发生了[3，2- b ]嘧啶9a，b，9a′，b′，10a，b。

  DOI：

  10.1002/jhet.5570330657
• 作为产物：
  描述：

  苯甲亚胺酸甲酯盐酸盐 在 lead(II) nitrate 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 5-imino-7-phenyl-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carbonitrile
  参考文献：
  名称：

  碳酸碳酸亚铵盐。XI †。由N-保护的2-甲硫基-1,3-噻嗪鎓盐和2-甲硫基噻唑鎓盐合成含N，S的杂环。第3部分。N保护的2-甲硫基-1,3-噻嗪鎓盐和2-甲硫基噻唑鎓盐与3-氨基-2-氰基-3-芳基丙烯腈的反应‡

  摘要：

  Ñ -Boc保护的2- memylthio -1,3-噻嗪1和2-methylthiothiazolium碘化物2,3从相应的3,4,5,6-四氢-2-获得ħ -1,3-噻嗪-2-硫酮和噻唑烷-2-硫酮在甲基碘的作用下与3-armno-2-cyano-3-芳基丙烯腈反应形成环状异硫脲5-7。用三氟乙酸除去保护基，然后将所需的环化成3,4-二氢-2 H，6 H-嘧啶基[ 2,1- b ] [1,3]噻嗪8a-c，8a'-c'和噻唑罗发生了[3，2- b ]嘧啶9a，b，9a′，b′，10a，b。

  DOI：

  10.1002/jhet.5570330657

文献信息

• One-Pot Synthesis of Thiazolidino [3,2-a] Pyrimidine Derivatives
  作者：Edwige Jeanneau-Nicolle、Martine Benoit-Guyod、Gérard Leclerc

  DOI：10.1080/00397919108016417

  日期：1991.7

  Abstract Reaction of 2-aminothiazoline with an aromatic aldehyde and an activated methylene group (malonitrile, diethylmalonate or ethylcyanoacetate) gave the title compounds. The structures are unambiguously assigned using spectroscopic data and chemical proofs.

  摘要 2-氨基噻唑啉与芳香醛和活化的亚甲基（丙二腈、丙二酸二乙酯或氰基乙酸乙酯）反应得到标题化合物。使用光谱数据和化学证明明确分配了这些结构。
• New thiazolo[3,2-a]pyrimidine derivatives, synthesis and structure-activity relationships
  作者：E Jeanneau-Nicolle、M Benoit-Guyod、A Namil、G Leclerc

  DOI：10.1016/0223-5234(92)90099-m

  日期：1992.3

  Twenty-six derivatives of 5- and 7-oxo or 5- and 7-aminothiazolo[3,2-a]pyrimidines were prepared and evaluated as positive inotropic, anti-inflammatory and antihypertensive agents both in vitro and in vivo. The structures of the 5- and 7-isomers have been confirmed unambiguously by IR, UV, H-1 and C-13 NMR and MS. The structure of 1a was confirmed by the synthesis of compound 1 whose structure had been previously established by X-ray analysis. The 5-aminothiazolo-pyrimidine-6-carbonitrile derivatives 5a and 5e exhibited potent inotropic activities. 5e was more potent than the classical reference amrinone. Three compounds 5e, 5i and 5j displayed moderate antihypertensive activities. The 4-chlorophenyl derivative 5d exhibited an anti-inflammatory activity 2-fold that of aspirin. This study has demonstrated that thiazolo[3,2-a]pyrimidine compounds have interesting biological potentialities, particularly as inotropic agents, a field which had never been explored so far for this series.
• Iminium carbonic acid derivative salts.<b>XI</b>. Synthesis of<i>N,S</i>-containing heterobicycles from<i>N</i>-protected 2-methylthio-1,3-thiazinium and 2-methylthiothiazoüum salts. Part 3. Reaction of<i>N</i>-protected 2-methylthio-1,3-thiazinium and 2-methylthiothiazolium salts with 3-amino-2-cyano-3-arylacrylonitriles
  作者：Wolfgang Hanefeld、Mahmoud Naeeni、Martin Schlitzer

  DOI：10.1002/jhet.5570330657

  日期：1996.11

  N-Boc-protected 2-memylthio-1,3-thiazinium 1 and 2-methylthiothiazolium iodides 2, 3 obtained from the corresponding 3,4,5,6-tetrahydro-2H-1,3-thiazine-2-thiones and thiazolidine-2-thiones by the action of methyl iodide were reacted with 3-armno-2-cyano-3-arylacrylonitriles forming the cyclic isothioureas 5–7. The protection group was removed with trifluoroacetic acid whereupon the desired cyclisation

  Ñ -Boc保护的2- memylthio -1,3-噻嗪1和2-methylthiothiazolium碘化物2,3从相应的3,4,5,6-四氢-2-获得ħ -1,3-噻嗪-2-硫酮和噻唑烷-2-硫酮在甲基碘的作用下与3-armno-2-cyano-3-芳基丙烯腈反应形成环状异硫脲5-7。用三氟乙酸除去保护基，然后将所需的环化成3,4-二氢-2 H，6 H-嘧啶基[ 2,1- b ] [1,3]噻嗪8a-c，8a'-c'和噻唑罗发生了[3，2- b ]嘧啶9a，b，9a′，b′，10a，b。