3-methylsulfanyl-5-cyano-12-oxopyrimido[4',5'-4,5]pyrido[2,1-b]benzothiazole

• 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: 3-methylsulfanyl-5-cyano-12-oxopyrimido[4',5'-4,5]pyrido[2,1-b]benzothiazole
• 英文别名: 5-Methylsulfanyl-9-oxo-17-thia-4,6,10-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1,3,5,7,11,13,15-heptaene-2-carbonitrile
• 化学式: C₁₅H₈N₄OS₂
• 分子量: 324.387
• InChiKey: APFAEGDUVKZNMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯并噻唑-2-乙腈 、 4-氯-2-甲硫基嘧啶-5-羧酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到3-methylsulfanyl-5-cyano-12-oxopyrimido[4',5'-4,5]pyrido[2,1-b]benzothiazole
  参考文献：
  名称：

  Reaction of 2-hetarylacetonitriles with ethyl 2-alkylsulfanyl-4-chloro-5-pyrimidinecarboxylates. Synthesis of new condensed pyrimidines

  摘要：

  Reactions of 2-hetarylacetonitriles 1 with ethyl 2-alkylsulfanyl-4-chloro-5-pyrimidinecarboxylates 4 were studied. The interaction of pyridine, benzimidazole and benzothiazole, derivatives 1a-d affords a series of new condensed pyridopyrimidines 5-7. In the case of benzoxazole- and 4-arylthiazole derivatives le-h ethyl 4-[(2-hetaryl)-cyano-methyl]-2-alkylsulfanylpyrimidine-5-carboxylates 9a-f were formed. Reactions of quinazoline derivatives 1i,k afford stable intermediates 9h,i which formed the cyclic compound 12 of angular structure in the presence of potash. The influence of the basicity of heterocycles and of steric factors on the intramolecular acylation reaction was studied. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00540-9

文献信息

• Reaction of 2-hetarylacetonitriles with ethyl 2-alkylsulfanyl-4-chloro-5-pyrimidinecarboxylates. Synthesis of new condensed pyrimidines
  作者：E.V Blyumin、Yu.M Volovenko、Hans Neunhoeffer、S.V Shishkina、R.A Zubatyuk、Oleg V Shishkin

  DOI：10.1016/s0040-4020(02)00540-9

  日期：2002.7

  Reactions of 2-hetarylacetonitriles 1 with ethyl 2-alkylsulfanyl-4-chloro-5-pyrimidinecarboxylates 4 were studied. The interaction of pyridine, benzimidazole and benzothiazole, derivatives 1a-d affords a series of new condensed pyridopyrimidines 5-7. In the case of benzoxazole- and 4-arylthiazole derivatives le-h ethyl 4-[(2-hetaryl)-cyano-methyl]-2-alkylsulfanylpyrimidine-5-carboxylates 9a-f were formed. Reactions of quinazoline derivatives 1i,k afford stable intermediates 9h,i which formed the cyclic compound 12 of angular structure in the presence of potash. The influence of the basicity of heterocycles and of steric factors on the intramolecular acylation reaction was studied. (C) 2002 Elsevier Science Ltd. All rights reserved.