ethyl 4-oxo-3-(4H-pyrimido<2,1-b>benzothiazole)carboxylate | 21786-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: ethyl 4-oxo-3-(4H-pyrimido<2,1-b>benzothiazole)carboxylate
• 英文别名: 3-ethoxycarbonyl-4H-pyrimido[2,1-b]benzothiazol-4-one；4-oxo-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylic acid ethyl ester；4-Oxopyrimido-<2,1-b>benzthiazol-3-carbonsaeureethylester；ethyl 4-oxo-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate；ethyl 4-oxopyrimido[2,1-b][1,3]benzothiazole-3-carboxylate
• CAS: 21786-89-0
• 化学式: C₁₃H₁₀N₂O₃S
• mdl: MFCD01460186
• 分子量: 274.3
• InChiKey: RSDYYXQTNJMYOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-oxo-3-(4H-pyrimido<2,1-b>benzothiazole)carboxylate 在 ammonium hydroxide 作用下， 反应 48.0h， 以85%的产率得到3-carboxamido-4H-pyrimido<2,1-b>benzothiazol-4-one
  参考文献：
  名称：

  Synthesis and benzodiazepine receptor binding of some 4H-pyrimido[2,1-b]benzothiazol-4-ones

  摘要：

  Synthesis and ability to displace [H-3]diazepam binding from rat brain membranes of the 3-(alkoxycarbonyl)-4H-pyrimido[2,1-b]benzothiazol-4-ones 3a-p and related compounds 10-12 are described. It has been found that some compounds bind to the benzodiazepine receptor (BZR) with potency greater than chlordiazepoxide. From a structure-affinity point of view the substitution at 6-position of pyrimido[2,1-b]benzothiazole nucleus was found conductive to higher affinity. In vitro data (GABA ratio) lend support to the fact that the most active compounds 3j, l might possess agonist properties at BZR.

  DOI：

  10.1016/0223-5234(92)90058-9
• 作为产物：
  描述：

  diethyl N-2-(benzothiazolyl)aminomethylenemalonate 生成 ethyl 4-oxo-3-(4H-pyrimido<2,1-b>benzothiazole)carboxylate
  参考文献：
  名称：

  Studies on Heterocyclic Compounds. XIII. Reaction of 2-Amino-benzazoles with Acetylenic Compounds

  摘要：

  报道了2-氨基苯并噻唑、2-氨基苯并噻唑、2-苯并恶唑和-苯并咪唑等2-氨基苯并唑与乙炔化合物的反应，并与这些苯并唑和乙氧基亚甲基丙二酸酯的缩合产物进行比较。在前一种情况下，得到2-氧代化合物，而4-氧代化合物是后一缩合中的产物。这些产物的结构通过核磁共振和质谱得到证实。

  DOI：

  10.1248/cpb.21.2019

文献信息

• Efficient regioselective synthesis of triheterocyclic compounds: imidazo[2,1-b]benzothiazoles, pyrimido[2,1-b]benzothiazolones and pyrimido[2,1-b]benzothiazoles
  作者：Cyrille Landreau、David Deniaud、Michel Evain、Alain Reliquet、Jean-Claude Meslin

  DOI：10.1039/b111639h

  日期：2002.3.8

  The preparation and characterisation of triheterocyclic compounds, via annulation reactions, are described. Amidines 1 reacted with substituted bromomethyl compounds, acid chlorides, and acrylic dienophiles to afford the corresponding imidazo[2,1-b]benzothiazoles 2 and pyrimido[2,1-b]benzothiazoles 3 or 4.

  通过环化反应制备和表征三杂环化合物的过程被详细描述。氨基脒1与取代的溴甲基化合物、酰氯以及丙烯二烯亲电试剂反应，得到了相应的咪唑并[2,1-b]苯并噻唑2以及嘧啶并[2,1-b]苯并噻唑3或4。
• The reactions of 2-aminothiazoles and 2-aminobenzothiazoles with propiolic acid and its esters
  作者：D. W. Dunwell、D. Evans

  DOI：10.1039/j39710002094

  日期：——

  The main products from the title reactions were 7H-thiazolo[3,2-a]pyrimidin-7-ones (IV) and 2H-pyrimido-[2,1-b]benzothiazol-2-ones (V). Treatment of some of these with primary and secondary aliphatic amines yielded 2-(β-aminoacryloyl)imino-Δ4-thiazolines (X) and the corresponding benzo-analogues (XI).

  标题反应的主要产物是7 H-噻唑并[3，2 - a ]嘧啶-7-酮（IV）和2 H-嘧啶-[ 2，1- b ]苯并噻唑-2-酮（V）。其中一些的伯和仲脂族胺处理得到2-（β-aminoacryloyl）亚氨基Δ 4 -thiazolines（X）和相应的苯并类似物（XI）。
• The synthesis of some 4<i>H</i>-pyrimido[2,1-<i>b</i>]benzothiazol-4-ones
  作者：Robert J. Alaimo

  DOI：10.1002/jhet.5570100515

  日期：1973.10

  A series of 8-substituted and 7,8-disubstituted-4-oxo-3-(4H-pyrimido[2,1-b]benzothiazole)carboxylic acids and esters including a 9-aza analog were synthesized from substituted 2-aminobenzothiazoles and diethyl ethoxymethylenemalonate. The 9-aza analog, ethyl 8-methoxy-4-oxo-3-(4H-pyrido[3′,2′:4,5]thiazolo[3,2-a]pyrimidine)carboxylate (56), represents the first preparation of this new heterocyclic ring

  由取代的2-氨基苯并噻唑合成了一系列的8-取代和7,8-二取代-4-氧代-3-（4 H-嘧啶[ 2,1- b ]苯并噻唑）羧酸和酯，包括9-氮杂类似物。和乙氧基亚甲基丙二酸二乙酯。9-氮杂类似物，乙基8-甲氧基-4-氧代-3-（4 H-吡啶基[3'，2'：4,5]噻唑并[3,2- a ]嘧啶）羧酸盐（56）首先准备这个新的杂环。检查了这些化合物的抗寄生虫活性，但是未检测到显着活性。
• Studies on Heterocyclic Compounds. XIII. Reaction of 2-Amino-benzazoles with Acetylenic Compounds
  作者：HARUO OGURA、MITSUO KAWANO、TSUNEO ITOH

  DOI：10.1248/cpb.21.2019

  日期：——

  Reaction of 2-aminobenzazoles such as 2-amino-benzothiazole, -benzoxazole, and-benzimidazole with acetylene compounds was reported comparing with the condensation product of these benzazoles and ethoxy methylenemalonate. In the former case, 2-oxo compounds were obtained while 4-oxo compounds were the product in the latter condensation. The structure of these products was confirmed from nuclear magnetic resonance and mass spectra.

  报道了2-氨基苯并噻唑、2-氨基苯并噻唑、2-苯并恶唑和-苯并咪唑等2-氨基苯并唑与乙炔化合物的反应，并与这些苯并唑和乙氧基亚甲基丙二酸酯的缩合产物进行比较。在前一种情况下，得到2-氧代化合物，而4-氧代化合物是后一缩合中的产物。这些产物的结构通过核磁共振和质谱得到证实。
• Fused pyrimidines as potential antimicrobic agents
  作者：Alfred Richardson、Frederick J. McCarty

  DOI：10.1021/jm00282a001

  日期：1972.12