5-acetyl-4-(2'-chlorophenyl)-6-methylpyrimidin-2(1H)-one | 1194097-19-2

• 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: 5-acetyl-4-(2'-chlorophenyl)-6-methylpyrimidin-2(1H)-one
• CAS: 1194097-19-2
• 化学式: C₁₃H₁₁ClN₂O₂
• 分子量: 262.696
• InChiKey: DJCXOOGSZNITEE-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  5-acetyl-4-(2-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one 以 乙腈 为溶剂， 反应 1.75h， 生成 5-acetyl-4-(2'-chlorophenyl)-6-methylpyrimidin-2(1H)-one
  参考文献：
  名称：

  光诱导的2-氧-1,2,3,4-四氢嘧啶-5-羧酰胺的脱氢反应

  摘要：

  通过将各种2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides（THPMs）暴露于紫外光下，研究其光敏性，以阐明位于4-上的取代基的性质的影响。杂环的5-位和氧气或氩气气氛对反应速率的影响。在氩气下的反应速率比在氧气下的反应速率更快，并且受THPM环4和5位上取代基的性质影响。此外，发现THPM-酰胺的脱氢比相应的5-乙氧基羰基-和5-乙酰基-THPM的脱氢更快。与溶液光化学相反，通过固态照射没有观察到变化。

  DOI：

  10.1007/s13738-012-0097-0

文献信息

• Light-induced Free Radical Oxidation of 2-Oxo-1,2,3,4-tetrahydropyrimidines
  作者：Hamid Reza Memarian、Leila Hejazi、Asadallah Farhadi

  DOI：10.1515/znb-2012-0313

  日期：2012.3.1

  A variety of 4-substituted 5-acetyl- and 5-carboethoxy-2-oxo-1,2,3,4-tetrahydropyrimidines were oxidized under UV irradiation in the presence or absence of benzoyl peroxide. The nature of the substituents on the 4- and 5-positions of the heterocyclic ring affects the rate of photo-oxidation, and irradiation of these compounds in the presence of benzoyl peroxide decreases the time of reaction drastically. Removal of 4-H by a benzoyloxy radical under formation of a trihydropyrimidinoyl radical intermediate occurs in the rate-determining step. The stability of this benzylic and allylic radical intermediate is affected by the nature and the position of the additional substituent on the phenyl group located at C-4.

  一系列4-取代的5-乙酰基和5-羧乙酯基-2-氧代-1,2,3,4-四氢嘧啶在紫外辐射下在有或无苯甲酰过氧化物存在下被氧化。杂环环上4-和5-位置的取代基的性质影响光氧化的速率，这些化合物在有苯甲酰过氧化物存在下的照射显著减少了反应时间。在速率决定步骤中，苯甲酰氧自由基去除4-H形成三氢嘧啶基自由基中间体。这种苄基和烯丙基自由基中间体的稳定性受到苯基团上附加取代基的性质和位置的影响，该苯基团位于C-4。
• Photo-oxidation of 5-acetyl-3,4-dihydropyrimidin-2(1H)-ones
  作者：Hamid Reza Memarian、Asadollah Farhadi、Hassan Sabzyan、Mousa Soleymani

  DOI：10.1016/j.jphotochem.2009.10.012

  日期：2010.1

  A variety of Biginelli 5-acetyl-3,4-dihydropyrimidin-2(1H)-ones are efficiently oxidized to their corresponding pyrimidin-2(1H)-one derivatives upon UV irradiation under argon atmosphere in chloroform solution. The nature of the additional substituent on the phenyl ring located on C-4 of the heterocyclic ring influences the rate of reaction. An electron-transfer induced photoreaction is proposed based

  在氩气中于氯仿溶液中紫外线照射后，各种Biginelli 5-乙酰基-3,4-二氢嘧啶-2（1H）-酮被有效氧化为相应的嘧啶-2（1H）-一衍生物。位于杂环的C-4上的苯环上的其他取代基的性质会影响反应速率。基于HCl和CH 2 Cl 2的形成，提出了电子转移诱导的光反应。
• Klingebiel, Uwe; Matthes, Christoph; Ringe, Arne, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2009, vol. 64, # 5, p. 532 - 540
  作者：Klingebiel, Uwe、Matthes, Christoph、Ringe, Arne、Magull, Joerg

  DOI：——

  日期：——
• Free-radical oxidation of 1,2,3,4-tetrahydro-2-oxopyrimidines
  作者：Hamid Reza Memarian、Nazanin Jafarpour、Asadallah Farhadi

  DOI：10.1007/s00706-011-0573-8

  日期：2012.2

  Free-radical oxidation of 4-substituted 5-acetyl- and 5-carboethoxy-1,2,3,4-tetrahydro-2-oxopyrimidines using benzoyl peroxide under thermal conditions has been investigated to elucidate the effects of the nature of the substituents in the 4- and 5-positions on the rate of reaction. Whereas the presence of the acetyl group instead of the carboethoxy group in position 5 decreases the rate of oxidation, the nature of the additional substituent (electron-releasing or electron-withdrawing group) and also its location on the phenyl ring attached to C-4 of the tetrahydropyrimidinone ring effectively influence the rate of reaction. The latter observation supports the proposal that the removal of the 4-hydrogen on the heterocyclic ring occurs in the rate-determining step.
• Ultrasound-assisted dehydrogenation of 5-acetyl-3,4-dihydropyrimidin-2(1H)-ones
  作者：Hamid Reza Memarian、Asadollah Farhadi、Hassan Sabzyan

  DOI：10.1016/j.ultsonch.2009.11.014

  日期：2010.3

  In this study, various 5-acetyl-3,4-dihydropyrimidin-2(1H)-ones were synthesized and the dehydrogenation of these compounds by potassium peroxydisulfate in aqueous acetonitrile under thermal and sono-thermal conditions were investigated. Whereas the effect of the nature of 4-substituent influences the rate of reaction, the application of sonic waves decreases drastically the time of thermal reaction. (c) 2009 Elsevier B.V. All rights reserved.