6-methoxypteridin-4(3H)-one | 16138-95-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 6-methoxypteridin-4(3H)-one
• 英文别名: 6-Methoxypteridin-4(3H)-one；6-methoxy-3H-pteridin-4-one
• CAS: 16138-95-7
• 化学式: C₇H₆N₄O₂
• 分子量: 178.15
• InChiKey: OFNZHNHXMOKULR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-methoxypteridin-4(3H)-one 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 异丙醇 为溶剂， 反应 13.0h， 生成 6-methoxy-N-(4-methoxyphenyl)pteridin-4-amine
  参考文献：
  名称：

  Synthesis ofN-Substituted-6-alkoxypteridin-4-amine

  摘要：

  A novel seven‐step methodology for the synthesis of N‐substituted‐6‐alkoxypteridin‐4‐amine has been developed with the total yields of 35.4–41%. Twenty new compounds were synthesized by heterocyclization of easily prepared 3‐amino‐6‐bromopyrazine‐2‐carboxamide, subsequent alkoxylation, chlorination, and nucleophilic substitution. Their structures were confirmed by 1H‐NMR, 13C‐NMR, ESI‐MS, and elemental analysis. The structure of N‐(3‐chloro‐4‐fluorophenyl)‐6‐ethoxypteridin‐4‐amine was further determined by X‐ray crystallographic analysis. It was found that different chlorinating reagents gave different products. The possible chlorination mechanism was discussed.

  DOI：

  10.1002/jhet.883
• 作为产物：
  描述：

  3-氨基吡嗪-2-羧酸 在 硫酸 、 氨 、 溴 、 sodium 、 乙酸酐 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 71.33h， 生成 6-methoxypteridin-4(3H)-one
  参考文献：
  名称：

  Synthesis ofN-Substituted-6-alkoxypteridin-4-amine

  摘要：

  A novel seven‐step methodology for the synthesis of N‐substituted‐6‐alkoxypteridin‐4‐amine has been developed with the total yields of 35.4–41%. Twenty new compounds were synthesized by heterocyclization of easily prepared 3‐amino‐6‐bromopyrazine‐2‐carboxamide, subsequent alkoxylation, chlorination, and nucleophilic substitution. Their structures were confirmed by 1H‐NMR, 13C‐NMR, ESI‐MS, and elemental analysis. The structure of N‐(3‐chloro‐4‐fluorophenyl)‐6‐ethoxypteridin‐4‐amine was further determined by X‐ray crystallographic analysis. It was found that different chlorinating reagents gave different products. The possible chlorination mechanism was discussed.

  DOI：

  10.1002/jhet.883

文献信息

• Electro-oxidative cyclization: access to quinazolinones <i>via</i> K₂S₂O₈ without transition metal catalyst and base
  作者：Yongzhi Hu、Huiqing Hou、Ling Yu、Sunying Zhou、Xianghua Wu、Weiming Sun、Fang Ke

  DOI：10.1039/d1ra05092c

  日期：——

  A K2S2O8-promoted oxidative tandem cyclization of primary alcohols with 2-aminobenzamides to synthesize quinazolinones was successfully achieved under undivided electrolytic conditions without a transition metal and base. The key feature of this protocol is the utilization of K2S2O8 as an inexpensive and easy-to-handle radical surrogate that can effectively promote the reaction via a simple procedure

  AK 2 S 2 O 8促进了伯醇与2-氨基苯甲酰胺的氧化串联环化以合成喹唑啉酮，在没有过渡金属和碱的不分电解条件下成功实现。该协议的主要特点是利用 K 2 S 2 O 8作为一种廉价且易于处理的自由基替代物，可以通过简单的程序有效地促进反应，从而通过形成氮杂环在恒定电流下以一锅法在室温下直接氧化环化。由于使用了连续流动的电化学装置，这种绿色、温和、实用的电合成具有高效率和优异的官能团耐受性，并且易于放大。
• Electrochemically induced synthesis of quinazolinones <i>via</i> cathode hydration of <i>o</i>-aminobenzonitriles in aqueous solutions
  作者：Li Yang、Huiqing Hou、Lan Li、Jin Wang、Sunying Zhou、Mei Wu、Fang Ke

  DOI：10.1039/d0ob02286a

  日期：——

  for the synthesis of substituted quinazolinones from simple and readily available o-aminobenzonitriles and aldehydes in water has been accomplished. I2/base and water play an unprecedented and vital role in the reaction. By electrochemically catalysed hydrolysis of o-aminobenzonitriles, the synthesis of quinazolinones with benzaldehyde was first proposed. The synthetic utility of this method was demonstrated

  已经实现了从水中的简单且容易获得的邻氨基苯甲腈和醛类合成取代的喹唑啉酮类的有效且实用的无催化过渡金属的方法。I 2 /碱和水在反应中起着前所未有的重要作用。通过电化学催化邻氨基苯甲腈的水解，首次提出了与苯甲醛合成喹唑啉酮的方法。该方法的合成效用通过克级操作以及生物活性N-（2,5-二氯苯基）-6-（2,2,2-三氟乙氧基）蝶呤-4-胺的制备得到证明。简单，实用且对环境无害的喹唑啉酮形成。
• Efficient and selective microwave-assisted copper-catalyzed synthesis of quinazolinone derivatives in aqueous
  作者：Fang Ke、Caiqin Liu、Peng Zhang、Jianhua Xu、Xiaole Chen

  DOI：10.1080/00397911.2018.1533974

  日期：2018.12.17

  Abstract Microwave-assisted copper-catalyzed cascade reactions between 2-halobenzoic acids and amidines to synthesize quinazolinone derivatives in water are reported. A variety of target products were obtained in good to excellent yields up to 94%. Its application was performed by the synthesis of 4-(1H-benzo[d]imidazol-2-ylthio)-6-methoxypteridine, which displayed significant anti-proliferation effect

  摘要 微波辅助铜催化 2-卤代苯甲酸和脒之间的级联反应在水中合成喹唑啉酮衍生物。获得了多种目标产品，产率高达 94%。其应用是通过合成4-(1H-苯并[d]咪唑-2-基硫基)-6-甲氧基蝶啶而进行的，具有显着的抗增殖作用。图形摘要
• Synthesis of<i>N</i>-Substituted-6-alkoxypteridin-4-amine
  作者：Chonggang Duan、Jiong Jia、Rongxiu Zhu、Jianwu Wang

  DOI：10.1002/jhet.883

  日期：2012.7

  A novel seven‐step methodology for the synthesis of N‐substituted‐6‐alkoxypteridin‐4‐amine has been developed with the total yields of 35.4–41%. Twenty new compounds were synthesized by heterocyclization of easily prepared 3‐amino‐6‐bromopyrazine‐2‐carboxamide, subsequent alkoxylation, chlorination, and nucleophilic substitution. Their structures were confirmed by 1H‐NMR, 13C‐NMR, ESI‐MS, and elemental analysis. The structure of N‐(3‐chloro‐4‐fluorophenyl)‐6‐ethoxypteridin‐4‐amine was further determined by X‐ray crystallographic analysis. It was found that different chlorinating reagents gave different products. The possible chlorination mechanism was discussed.