6-Amino-3-phenyl-pyrazolo<5,1-b>thiazol-7-carbonitril | 112085-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-Amino-3-phenyl-pyrazolo<5,1-b>thiazol-7-carbonitril
• 英文别名: 6-Amino-3-phenylpyrazolo[5,1-b][1,3]thiazole-7-carbonitrile
• CAS: 112085-24-2
• 化学式: C₁₂H₈N₄S
• 分子量: 240.288
• InChiKey: WUBHNWVMFKGCBW-UHFFFAOYSA-N

物化性质

• 熔点：
  189-191 °C(Solv: ethanol (64-17-5))
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-amino-4-phenylthiazoline-2(3H)-thione 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.33h， 生成 6-Amino-3-phenyl-pyrazolo<5,1-b>thiazol-7-carbonitril
  参考文献：
  名称：

  Fused Thiazoles from 3-Amino-thiazoline-2-thiones: Synthesis of Pyrazolo[5,1-b]thiazole and Thiazolo[2,3-b]-1,3,4-thiadiazine Derivatives

  摘要：

  DOI：

  10.3987/r-1987-05-1323

文献信息

• Amino-thieno[2,3-c]pyrazole und Amino-thieno[2,3-b]pyrrole
  作者：K. Gewald、S. Rennert、R. Schindler、H. Sch�fer

  DOI：10.1002/prac.199533701101

  日期：——

  The synthesis of thieno[2,3-c]pyrazoles and thieno [2,3-b]pyrroles is described. From the dithioliumsalt (1) and potassium hydroxide the potassium-(2,2-dicyan-1-methylthio-ethen-1-yl)-thiolate (2) is formed. This reacts with hydrazine hydrate to form the 3-amino-5-thioxo-pyrazol-4-carbonitrile (3). S-Alkylation with alpha-chlorocarbonyl compounds yielding (6a-c) leads via Thorpe-Ziegler-cyclization to 3,4-diamino-thieno[2,3-c]pyrazoles (9) if the position 1 is alkylated (8). Acetyl acetone yields 2-mercapto-pyrazolo[1,5-a]pyrimidine (5). After S-alkylation (10a-d) are immediately cyclized to thieno [2',3':3,4]pyrazolo[1,5-a]pyrimidine (11a-d). The ketone (6a) can be cyclized to the pyrazolo [5,1-b]thiazole (12). 3 reacts with oxalyl chloride to form the 2,3-dioxo-6-thioxo-imidazo[1,2-b]pyrazole (13) of which S-phenacyl derivative (14) because the NH-proton cannot be cyclized. The 5-amino-3,4-dicyano-pyrrol-2-thiolate (16) shows the analogous behaviour. The S-alkylation is followed by cyclization, and 3,5-diamino-thieno[2,3-b]pyrroles (18a-b) arise. Reaction of 5-amino-2-alkylthio-pyrrol-3,5-dicarbonitrile (17) with acetyl acetone provides pyrrolo[1,2-a]pyrimidine (20a-c) which can be cyclized to form thieno[3',2':4,6]pyrimidines (21a-c) very easily.
• MOLINA, PEDRO;ARQUES, ANTONIO;VELASCO, MARIA DE LOS DESAMPARADOS;VILLALGO+, HETEROCYCLES, 26,(1987) N 5, 1323-1332
  作者：MOLINA, PEDRO、ARQUES, ANTONIO、VELASCO, MARIA DE LOS DESAMPARADOS、VILLALGO+

  DOI：——

  日期：——
• Fused Thiazoles from 3-Amino-thiazoline-2-thiones: Synthesis of Pyrazolo[5,1-b]thiazole and Thiazolo[2,3-b]-1,3,4-thiadiazine Derivatives
  作者：Pedro Molina、Antonio Arques、Maria de los Desamparados Velasco、Jos� Manuel Villalgordo

  DOI：10.3987/r-1987-05-1323

  日期：——