3-(4-chlorobenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione | 1289383-46-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(4-chlorobenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione
• 英文别名: 3-(4-chlorobenzoyl)-5H-pyrrolo[1,2-a]quinoxaline-1,2,4-trione
• CAS: 1289383-46-5
• 化学式: C₁₈H₉ClN₂O₄
• 分子量: 352.733
• InChiKey: IYTHTHFTMVCDES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-chlorobenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione 以 diphenyl ether-biphenyl eutectic 为溶剂， 以95%的产率得到3-(4-chlorobenzoyl)furo[3,2-b]quinoxalin-2(4H)-one
  参考文献：
  名称：

  Five-membered 2,3-dioxoheterocycles: LXXIII. Synthesis and thermolysis of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones

  摘要：

  Reactions of (Z)-3-(phenacylidene-2-oxo)-3,4-dihydroquinoxalin-2(1H)-ones and (Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydroquinoxalin-2(1H)-one with oxalyl chloride led to the formation of 3-acyl-1H-pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones that at the thermal decarbonylation generated acyl(3-oxoquinoxalin-2-yl)ketenes which underwent the intramolecular stabilization giving 3-acylfuro[3,2-b]quinoxalin-2(4H)-ones.

  DOI：

  10.1134/s1070428011020151
• 作为产物：
  描述：

  甲基 4-(4-氯苯基)-2,4-二羰基丁酸 以 1,4-二氧六环 、 氯仿 为溶剂， 生成 3-(4-chlorobenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione
  参考文献：
  名称：

  Five-membered 2,3-dioxoheterocycles: LXXIII. Synthesis and thermolysis of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones

  摘要：

  Reactions of (Z)-3-(phenacylidene-2-oxo)-3,4-dihydroquinoxalin-2(1H)-ones and (Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydroquinoxalin-2(1H)-one with oxalyl chloride led to the formation of 3-acyl-1H-pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones that at the thermal decarbonylation generated acyl(3-oxoquinoxalin-2-yl)ketenes which underwent the intramolecular stabilization giving 3-acylfuro[3,2-b]quinoxalin-2(4H)-ones.

  DOI：

  10.1134/s1070428011020151

文献信息

• Alkaloid-like annulated pyrano[4,3-b]pyrroles: antiviral activity and hydrolysis
  作者：Ekaterina E. Khramtsova、Maksim V. Dmitriev、Nikolay I. Bormotov、Olga А. Serova、Larisa N. Shishkina、Andrey N. Maslivets

  DOI：10.1007/s10593-021-02928-0

  日期：2021.4

  Alkaloid-like angular 6/6/5/6-annulated pyrano[4,3-b]pyrroles (pretazettine analogs) contain chemically labile groups that can react with water at room temperature. Their antiviral activity against Vaccinia virus and their tendency to hydrolysis were investigated. Compounds that were more resistant to hydrolysis exhibited the greatest antiviral activity.

  类生物碱的角6/6/5/6型环吡喃并[4,3- b ]吡咯（Pretazettine类似物）包含化学不稳定的基团，可在室温下与水反应。研究了它们对牛痘病毒的抗病毒活性及其水解趋势。更耐水解的化合物表现出最大的抗病毒活性。
• Synthesis of Pyrano[4′,3′:2,3]pyrrolo[1,2-a]quinoxalines by Reaction of Aroylpyrroloquinoxalines with Alkyl Vinyl Ethers
  作者：S. O. Kasatkina、M. S. Titov、E. E. Stepanova、M. V. Dmitriev、A. N. Maslivets

  DOI：10.1134/s1070428018040188

  日期：2018.4

  Thermally induced [4 + 2]-cycloaddition of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with alkyl vinyl ethers afforded mixtures of diastereoisomeric (5S*,6aR*)- and (5R*,6aR*)-5-alkoxy-3-aryl-5,6-dihydropyrano[ 4′,3′: 2,3]pyrrolo[1,2-a]quinoxaline-1,2,7(8H)-triones.

  3-芳基吡咯并[1,2- a ]喹喔啉-1,2,4（5 H）-三酮与烷基乙烯基醚的热诱导[4 + 2]-环加成反应得到非对映异构体（5 S *，6a R *）的混合物-和（5 R *，6a R *）-5-烷氧基-3-芳基-5,6-二氢吡喃并[4'，3'：2,3]吡咯并[1,2- a ]喹喔啉-1,2， 7（8 H）-三酮。
• A facile approach to spiro[dihydrofuran-2,3'-oxindoles] via formal [4 + 1] annulation reaction of fused 1<i>H</i>-pyrrole-2,3-diones with diazooxindoles
  作者：Pavel A Topanov、Anna A Maslivets、Maksim V Dmitriev、Irina V Mashevskaya、Yurii V Shklyaev、Andrey N Maslivets

  DOI：10.3762/bjoc.18.162

  日期：——

  There has been developed an easy synthetic approach to spiro[dihydrofuran-2,3'-oxindoles] via a highly diastereoselective formal [4 + 1] cycloaddition reaction of [e]-fused 1H-pyrrole-2,3-diones with diazooxindoles. The described novel heterocyclic systems are heteroanalogues of antimicrobial and antibiofilm fungal metabolites. The developed reaction represents the first example of involving 1H-pyrrole-2

  通过 [ e ]-稠合 1 H -pyrrole-2,3-diones 与 diazooxindoles的高度非对映选择性 [4 + 1] 环加成反应，开发了一种简单的螺 [dihydrofuran-2,3'-oxindoles] 合成方法. 所描述的新型杂环系统是抗菌和抗生物膜真菌代谢物的杂类似物。开发的反应代表了在 [4 + 1] 环化反应中在 [ e ]侧融合 1 H -pyrrole-2,3-diones的第一个例子。
• Reaction of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with arylhydrazines
  作者：I. V. Mashevskaya、N. V. Suchkova、L. V. Kuslina、A. N. Maslivets

  DOI：10.1134/s1070428015090158

  日期：2015.9

  3-Aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones reacted with arylhydrazines to give substituted (Z)-2-(2-arylhydrazinylidene)-3-aroylpyrrolo[1,2-a]quinoxaline-1,4(2H,5H)-diones and (Z)-5-aryl-1-arylamino- 5-hydroxy-4-[3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene]pyrrolidine-2,3-diones.
• Reaction of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with quinaldine and substituted quinoxalines
  作者：V. V. Konovalova、Yu. V. Shklyaev、A. N. Maslivets

  DOI：10.1134/s1070428015050176

  日期：2015.5

  3-Aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones react with quinaldine and substituted 2-methylquinoxalines affording 3-aroyl-2-hydroxy-3a-(quinolin-2-ylmethyl)pyrrolo[1,2-a]quinoxaline-1,4-(3aH,5H)-diones and 3-aroyl-2-hydroxy-3a-(quinoxalin-2-ylmethyl)pyrrolo[1,2-a]quinoxaline-1,4-(3aH,5H)-diones respectively.