6-(2-chloro-6-ethoxypyridin-4-yl)-1,2,3,4-tetrahydro-2-oxo-4-(2-thienyl)pyrimidine | 1160150-78-6

• 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: 6-(2-chloro-6-ethoxypyridin-4-yl)-1,2,3,4-tetrahydro-2-oxo-4-(2-thienyl)pyrimidine
• 英文别名: 6-[(2-Chloro-6-ethoxypyridin-4-yl)]-1,2,3,4-tetrahydro-2-oxo-4-(2-thienyl)pyrimidine；6-(2-chloro-6-ethoxypyridin-4-yl)-4-thiophen-2-yl-3,4-dihydro-1H-pyrimidin-2-one
• CAS: 1160150-78-6
• 化学式: C₁₅H₁₄ClN₃O₂S
• 分子量: 335.814
• InChiKey: NBXGDBXCUPXZPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  尿素 、 1-(2-氯-6-乙氧基吡啶-4-基)-3-(噻吩-2-基)丙-2-烯-1-酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以65%的产率得到6-(2-chloro-6-ethoxypyridin-4-yl)-1,2,3,4-tetrahydro-2-oxo-4-(2-thienyl)pyrimidine
  参考文献：
  名称：

  Synthesis, and analgesic and antiparkinsonian activities of thiopyrimidine, pyrane, pyrazoline, and thiazolopyrimidine derivatives from 2-chloro-6-ethoxy-4-acetylpyridine

  摘要：

  A series of substituted pyridine derivatives were prepared from 2-chloro-6-ethoxy-4-acetylpyridine, which was prepared from the corresponding citrazinic acid as starting material. Reaction of acetylpyridine with thiophene-2-carboxaldehyde afforded the 2-chloro-6-ethoxy-4-beta-(2-thienyl)acryloylpyridine, which was reacted with malononitrile in refluxing ethanol in the presence of piperidine as a catalyst to afford the cyanoaminopyrane derivative. Acryloylpyridine was treated with urea or guanidine hydrochloride in refluxing ethanolic potassium hydroxide to give the corresponding pyrimidinone and aminopyrimidine derivatives. The latter was condensed with hydrazine hydrate or phenyl hydrazine to give pyrazoline and N-phenylpyrazoline derivatives. Finally, cycloaddition reaction of acryloylpyridine with thiourea yielded thioxopyrimidine, which was treated with 2-bromopropionic acid, 3-bromopropionic acid, or bromoacetic acid to yield methylthiazolo-, thiazino-, and thiazolopyrimidine derivatives. The arylmethylene derivative was prepared by reacting thiazolopyrimidine with benzaldehyde or by reacting thioxopyrimidine with benzaldehyde and bromoacetic acid in one step. The pharmacological screening showed that many of these compounds have good analgesic and antiparkinsonian activities comparable to Valdecoxib (R) and Benzatropine (R) as reference drugs.

  DOI：

  10.1007/s00706-008-0937-x

文献信息

• Synthesis, and analgesic and antiparkinsonian activities of thiopyrimidine, pyrane, pyrazoline, and thiazolopyrimidine derivatives from 2-chloro-6-ethoxy-4-acetylpyridine
  作者：Abd El-Galil E. Amr、Soher S. Maigali、Mohamed M. Abdulla

  DOI：10.1007/s00706-008-0937-x

  日期：2008.11

  A series of substituted pyridine derivatives were prepared from 2-chloro-6-ethoxy-4-acetylpyridine, which was prepared from the corresponding citrazinic acid as starting material. Reaction of acetylpyridine with thiophene-2-carboxaldehyde afforded the 2-chloro-6-ethoxy-4-beta-(2-thienyl)acryloylpyridine, which was reacted with malononitrile in refluxing ethanol in the presence of piperidine as a catalyst to afford the cyanoaminopyrane derivative. Acryloylpyridine was treated with urea or guanidine hydrochloride in refluxing ethanolic potassium hydroxide to give the corresponding pyrimidinone and aminopyrimidine derivatives. The latter was condensed with hydrazine hydrate or phenyl hydrazine to give pyrazoline and N-phenylpyrazoline derivatives. Finally, cycloaddition reaction of acryloylpyridine with thiourea yielded thioxopyrimidine, which was treated with 2-bromopropionic acid, 3-bromopropionic acid, or bromoacetic acid to yield methylthiazolo-, thiazino-, and thiazolopyrimidine derivatives. The arylmethylene derivative was prepared by reacting thiazolopyrimidine with benzaldehyde or by reacting thioxopyrimidine with benzaldehyde and bromoacetic acid in one step. The pharmacological screening showed that many of these compounds have good analgesic and antiparkinsonian activities comparable to Valdecoxib (R) and Benzatropine (R) as reference drugs.