5-methyl-3-phenyl-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one | 31703-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methyl-3-phenyl-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
• 英文别名: 5-methyl-3-phenyl-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
• CAS: 31703-13-6
• 化学式: C₁₁H₉N₅O
• 分子量: 227.225
• InChiKey: QJRDVYMEQSOURY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.81
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  76.46
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-methyl-3-phenyl-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one 在 三氯化铝 、 magnesium oxide 、 palladium dichloride 盐酸 、 氢气 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 98.5h， 生成 5-acetamido-α-benzamido-1-phenyl-1H-1,2,3-triazole-4-acetonitrile
  参考文献：
  名称：

  Higashino, Takeo; Sato, Susumu; Miyashita, Akira, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 12, p. 4803 - 4812

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氨基-1-苯基-1H-1,2,3-三唑-4-甲酰胺 、 sodium ethanolate 以 乙醇 、 乙酸乙酯 为溶剂， 反应 20.0h， 以78%的产率得到5-methyl-3-phenyl-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
  参考文献：
  名称：

  Higashino, Takeo; Sato, Susumu; Miyashita, Akira, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 12, p. 4803 - 4812

  摘要：

  DOI：

文献信息

• Catalytic Action of Azolium Salts. IX. Synthesis of 6-Aroyl-9H-purines and Their Analogues by Nucleophilic Aroylation Catalyzed by Imidazolium or Benzimidazolium Salt.
  作者：Akira MIYASHITA、Yumiko SUZUKI、Ken-ichi IWAMOTO、Takeo HIGASHINO

  DOI：10.1248/cpb.46.390

  日期：——

  In the presence of 1, 3-dimethylimidazolium iodide (1), 6-chloro-9-phenyl-9H-purine (7) and 4-chloro-5, 6-dimethylpyrrolo[2, 3-d]pyrimidines 40-42 undrwent uncleophilic aroylation with arenecarbaldehydes (5) to give the corresponding fused aroylpyrimidines 8 and 43-45. 1, 3-Dimethylbenzimidazolium iodide (2) was an effective catalyst for the similar synthesis of 7-aroyl-3-phenyl-3H-1, 2, 3-triazolo[4, 5-d]pyrimidines 16-21. In the synthesis of 4-aroyl-1H-pyrazolo[3, 4-d]pyrimidines 26-32, both azolium salts 1 and 2 were effective as catalysts. Moreover, 4-aroyl-7H-pyrrolo[2, 3-d]pyrimidines 43-45 were obtained in good yields via the 4-tosyl derivatives, in the presence of catalytic amounts of sodium p-toluenesulfinate (46) and the imidazolium salt 1. This catalytic aroylation was found to be a facile and useful method for the synthesis of 6-aroyl-9H-purines and their analogues.

  在1, 3-二甲基咪唑鎓碘化物（1）的存在下，6-氯-9-苯基-9H-嘌呤（7）和4-氯-5, 6-二甲基吡咯并[2, 3-d]嘧啶（40-42）与芳烃醛（5）发生亲核芳酰化反应，生成相应的融合芳酰嘧啶（8和43-45）。1, 3-二甲基苯并咪唑鎓碘化物（2）是合成7-酰基-3-苯基-3H-1, 2, 3-三唑并[4, 5-d]嘧啶（16-21）的有效催化剂。在合成4-酰基-1H-吡唑并[3, 4-d]嘧啶（26-32）中，咪唑盐（1和2）均表现出良好的催化效果。此外，通过4-托磺酸衍生物，在催化量的对甲苯磺酸钠（46）和咪唑盐（1）的存在下，获得了良好产率的4-酰基-7H-吡咯并[2, 3-d]嘧啶（43-45）。这种催化芳酰化反应被发现是一种简便而有效的方法，用于合成6-酰基-9H-嘌呤及其类似物。
• Three-Step Synthetic Pathway toward Fully Decorated [1,2,3]Triazolo[4,5-<i>d</i>]pyrimidine (8-Azapurine) Derivatives
  作者：Felien Reniers、Stijn Anthonissen、Luc Van Meervelt、Wim Dehaen

  DOI：10.1021/acs.orglett.3c00729

  日期：2023.4.28

  5-d]pyrimidines (8-azapurines) are known bioisosteres of the purine nucleus. A step-efficient synthesis of 8-azapurines, in particular 6-alkyl derivatives, is currently unavailable. This work focuses on a three-step synthetic pathway for the synthesis of fully decorated 8-azapurines, with special attention on 6-alkyl-8-azapurines. A diverse library of 8-azapurines was obtained starting from various alkynes

  [1,2,3]三唑并[4,5- d ]嘧啶（8-氮杂嘌呤）是已知的嘌呤核生物电子等排物。目前无法有效地合成 8-氮杂嘌呤，特别是 6-烷基衍生物。这项工作侧重于合成完全修饰的 8-氮杂嘌呤的三步合成途径，特别关注 6-烷基-8-氮杂嘌呤。从各种炔烃、叠氮化物和脒开始，获得了一个多样化的 8-氮杂嘌呤库，涉及中断的 CuAAC、氧化和环化反应。此外，对选定数量的底物进行了后功能化反应。
• Synthesis of Fused Pyrimidinones by Reaction of Aminoarenecarboxamide with Esters; Preparation of Pyrrolo[2,3-d]-, Thieno[2,3-d]-, Isoxazolo[5,4-d]-, and 1,2,3-Triazolo[4,5-d]-pyrimidinones, and Quinazoles
  作者：Akira Miyashita、Katsuhiro Fujimoto、Tomomi Okada、Takeo Higashino

  DOI：10.3987/com-95-s75

  日期：——

  Several fused pyrimidinones were synthesized by reaction of aminoarenecarboxamide with esters in moderate to good yields. In the presence of sodium ethoxide, treatments of 2-amino-1-phenyl-3-pyrrolecarboxamide(4, 5, and 6), 2-amino-3-thiophene-carboxamide (14), 3-amino-4-isoxazolecarboxamide (10 and 11), 4-amino-1,2,3-triazole-5-carboxamide (16), and o-aminobenzamide (18) with esters (3) such as ethyl formate (3a) and ethyl acetate (3b) led to the corresponding pyrrolo[2,3-d]- (7, 8, and 9), and thieno[2,3-d]pyrimidin-4(3H)-ones (15), isoxazolo[5,4-d]pyrimidin-4(5H)-ones (12 and 13), 1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-ones (17), and 4(3H)-quinazolones (19), respectively.
• HIGASHINO, TAKEO;SATO, SUSUMU;MIYASHITA, AKIRA;KATORI, TATSUHIKO, CHEM. AND PHARM. BULL., 35,(1987) N 12, 4803-4812
  作者：HIGASHINO, TAKEO、SATO, SUSUMU、MIYASHITA, AKIRA、KATORI, TATSUHIKO

  DOI：——

  日期：——