2,3-dimethylpyrrolo[1,2-a]pyrazin-1(2H)-one | 116212-50-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡嗪类
• 英文名称: 2,3-dimethylpyrrolo[1,2-a]pyrazin-1(2H)-one
• 英文别名: 1-Oxo-2,3-dimethylpyrrolo[1,2-a]pyrazine；2,3-dimethylpyrrolo[1,2-a]pyrazin-1-one
• CAS: 116212-50-1
• 化学式: C₉H₁₀N₂O
• 分子量: 162.191
• InChiKey: PQNFTRUZFNCYEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 在 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.67h， 生成 2,3-dimethylpyrrolo[1,2-a]pyrazin-1(2H)-one
  参考文献：
  名称：

  Selective synthesis of N-substituted pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives via alkyne cyclization

  摘要：

  A novel and efficient synthesis of N-substituted pyrrolo-pyrazinone derivatives has been developed. A trichloroacetyl group connected to the pyrrole ring was converted into the desired carboxamide derivatives. Promoted by NaH, the pyrrole carboxamide derivatives underwent a tandem reaction with propargyl bromide to afford pyrrolo-pyrazinones with high efficiency under very mild conditions. The mechanism for the formation of the products is discussed and supported by DFT calculations. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.10.044

文献信息

• Mechanistic Insights into the Reaction of <i>N</i> ‐Propargylated Pyrrole‐ and Indole‐Carbaldehyde with Ammonia, Alkyl Amines, and Branched Amines: A Synthetic and Theoretical Investigation
  作者：Ozlem Sari、Ali Fatih Seybek、Serdal Kaya、Nurettin Menges、Safiye Sag Erdem、Metin Balci

  DOI：10.1002/ejoc.201900084

  日期：2019.9

  TOC Text: Reactions of N‐propargylated pyrrole and indole carbaldehydes with different types of amines were investigated. The nature of products was determined by the type of amine used. The reaction with alkylamines formed the corresponding pyrazinone derivatives, while branched amines led to the formation of indolizine derivatives. The reaction mechanisms were studied by computational methods.

  TOC文本：研究了N-炔丙基化吡咯和吲哚甲醛与不同类型胺的反应。产品的性质取决于所用胺的类型。与烷基胺的反应形成了相应的吡嗪酮衍生物，而支链胺导致了吲哚嗪衍生物的形成。通过计算方法研究了反应机理。
• A concise synthesis of peramine, a metabolite of endophytic fungi
  作者：Shinsaku Ito、Yuta Yamamoto、Toshio Nishikawa

  DOI：10.1080/09168451.2018.1511966

  日期：2018.12.2

  The total synthesis of peramine, a natural product isolated from an endophytic fungi, has been achieved in four steps and 34% overall yield from known compounds. The key step was the one-pot construction of the pyrrolopyrazinone ring from pyrrole amide and propargyl bromide. The preparation of peramine-d4 as an internal standard for quantitative analysis by MS is also described.

  从胺类化合物中分离出来的天然产物过胺的总合成过程已经完成了四个步骤，从已知化合物中获得的总收率为34％。关键步骤是由吡咯酰胺和炔丙基溴一锅构建吡咯并吡嗪酮环。还描述了过胺-d4的制备方法，作为内标通过MS进行定量分析。
• Total synthesis of peramine
  作者：Donald J. Dumas

  DOI：10.1021/jo00255a002

  日期：1988.9
• DUMAS, DONALD J., J. ORG. CHEM., 53,(1988) N 20, C. 4650-4653
  作者：DUMAS, DONALD J.

  DOI：——

  日期：——
• Selective synthesis of N-substituted pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives via alkyne cyclization
  作者：Yasin Çetinkaya、Metin Balci

  DOI：10.1016/j.tetlet.2014.10.044

  日期：2014.12

  A novel and efficient synthesis of N-substituted pyrrolo-pyrazinone derivatives has been developed. A trichloroacetyl group connected to the pyrrole ring was converted into the desired carboxamide derivatives. Promoted by NaH, the pyrrole carboxamide derivatives underwent a tandem reaction with propargyl bromide to afford pyrrolo-pyrazinones with high efficiency under very mild conditions. The mechanism for the formation of the products is discussed and supported by DFT calculations. (C) 2014 Elsevier Ltd. All rights reserved.