2,2'-bis(methylthio)-3H-spiro[pyrimido[4,5-b]quinoline-5,5'-pyrrolo[2,3-d]pyrimidine]-4,4',6'(3'H,7'H,10H)-trione | 1043252-22-7

• 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: 2,2'-bis(methylthio)-3H-spiro[pyrimido[4,5-b]quinoline-5,5'-pyrrolo[2,3-d]pyrimidine]-4,4',6'(3'H,7'H,10H)-trione
• 英文别名: 2,2'-Bis(methylsulfanyl)spiro[3,10-dihydropyrimido[4,5-b]quinoline-5,5'-3,7-dihydropyrrolo[2,3-d]pyrimidine]-4,4',6'-trione
• CAS: 1043252-22-7
• 化学式: C₁₈H₁₄N₆O₃S₂
• 分子量: 426.48
• InChiKey: ZOWWRVJSJJLIEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  175
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2'-bis(methylthio)-3H-spiro[pyrimido[4,5-b]quinoline-5,5'-pyrrolo[2,3-d]pyrimidine]-4,4',6'(3'H,7'H,10H)-trione 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 叔丁醇 为溶剂， 以32%的产率得到2,2'-bis(methylthio)-7',7a',10,10a-tetrahydro-3H-spiro-[pyrimido[4,5-b]quinoline-5,5'-pyrrolo[2,3-d]pyrimidine]-4,4',6'(3'H,4aH,4a'H)-trione
  参考文献：
  名称：

  Identification and optimization of novel pyrimido-isoxazolidine and oxazine as selective hydride donors

  摘要：

  Two novel carbon skeletons (3S,3a'R)-6'-(methylthio)-5',7a'-dihydro-1'H-spiro[indoline-3,3'-isoxazolo [3,4-d]pyrimidine]-2,4'(3a'H)-dione (11a) and 3-(methylthio)-4a,5,7,11c-tetrahydropyrimido[4',5':3,4] [1,2]oxazino[6,5-b]indol-1(2H)-one (12a) are characterized as hydride donors. The generation of these hydride sources during the spiroannulation reaction between isatin (4) and pyrimidine (5) through the free radical mechanism, was confirmed by (i) the increase in the stoichiometric yields of 11 and 12 when the same reaction was carried out in the presence of free radical initiators (e.g., mCPBA) and (ii) the formation of oxazepine (14) when AIBN was used as free radical initiator. The PKIE [K-H/K-D] values 4.5 and 4.9 obtained when deuterated 11a (d) was used in the presence of TFA and TFA-d, respectively, suggest the hydride transfer step to be the rate determining step. These hydrides donors selectively reduce aldehyde in the presence of other reducible groups. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.105
• 作为产物：
  描述：

  基巯基-4-氨基-6-羟基嘧啶 、 靛红 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以73%的产率得到2,2'-bis(methylthio)-3H-spiro[pyrimido[4,5-b]quinoline-5,5'-pyrrolo[2,3-d]pyrimidine]-4,4',6'(3'H,7'H,10H)-trione
  参考文献：
  名称：

  6-氨基尿嘧啶和靛红的新型反应

  摘要：

  报道了一种简单新颖的6-氨基尿嘧啶和靛红的环缩合反应，用于合成螺[pyrimido [4,5 - b ]喹啉-5,5'-pyrrolo [2,3- d ]嘧啶]衍生物。

  DOI：

  10.1016/j.tet.2008.05.063

文献信息

• Clean Synthesis and Antibacterial Activities of Spiro[pyrimido[4,5-b]quinoline-5,5'-pyrrolo[2,3-d]pyrimidine]-pentaones
  作者：Ramin Ghahremanzadeh、Seyyedeh Cobra Azimi、Nader Gholami、Ayoob Bazgir

  DOI：10.1248/cpb.56.1617

  日期：——

  A simple, clean and efficient method for the synthesis of spiro[pyrimido[4,5-b]quinoline-5,5'-pyrrolo[2,3-d]pyrimidine]-pentaone derivatives by condensation reaction of 6-amino-uracils and isatins in aqueous media is reported. These products were evaluated in vitro for their antibacterial activities.

  通过6-氨基-尿嘧啶的缩合反应合成螺[pyrimido [4,5-b]喹啉-5,5'-吡咯并[2,3-d]嘧啶]-戊酮衍生物的简单，干净，有效的方法并报道了水性介质中的isatins。在体外评估了这些产品的抗菌活性。