2-imino-2H-1-benzopyran-3-carboxamide | 52218-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-imino-2H-1-benzopyran-3-carboxamide
• 英文别名: 2-imino-2H-chromene-3-carboxamide；2-iminocoumarin-3-carboxamide；2-iminochromene-3-carboxamide
• CAS: 52218-17-4
• 化学式: C₁₀H₈N₂O₂
• mdl: MFCD00488488
• 分子量: 188.186
• InChiKey: APPXOPKWRCEMGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-imino-2H-1-benzopyran-3-carboxamide 在 tetraphosphorus decasulfide 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以95%的产率得到2-sulfanyl-2-sulfido-2,3-dihydro-4H-chromeno[2,3-d][1,3,2]diazaphosphinin-4-one
  参考文献：
  名称：

  Reaction of 2-imino-2H-chromene-3-carboxamide with phosphorus sulfides: Synthesis of novel 2-sulfido-2,3-dihydro-4H-chromeno[2,3-d][1,3,2]diaza-phosphinines

  摘要：

  Novel 2-sulfido-2,3-dihydro-4H-chromeno[2,3-d][1,3,2]diazaphosphinines are obtained in a simple one-pot procedure via treatment of 2-imino-2H-chromene-3-carboxamide with various phosphorus sulfides. Possible reaction mechanisms are proposed. The structure of the obtained products is confirmed by elemental analyses and spectral tools.[GRAPHICS].

  DOI：

  10.1080/10426507.2018.1487439
• 作为产物：
  描述：

  水杨醛 以64%的产率得到
  参考文献：
  名称：

  Burke (Jr) Terrence R., Lim Benjamin, Marquez Victor E., Li Zhen-Hong, Bo+, J. Med. Chem., 36 (1993) N 4, S 425-432

  摘要：

  DOI：
• 作为试剂：
  描述：

  乙酰乙酰胺 在 哌啶 、 2-imino-2H-1-benzopyran-3-carboxamide 作用下， 反应 2.0h， 以11%的产率得到2-methyl-4,5-dioxo-3H-chromeno[3,4-c]pyridine-1-carboxamide
  参考文献：
  名称：

  O'Callaghan, Conor N.; McMurry, T. Brian H.; O'Brien, John E., Journal of Chemical Research, Miniprint, 1997, # 2, p. 453 - 474

  摘要：

  DOI：

文献信息

• Activated Nitriles in Heterocyclic Synthesis. Novel Synthesis of 5-Imino-5<i>H</i>-[1]benzopyrano[3,4-<i>c</i>]pyridine-4(3<i>H</i>)-thiones and Their Oxo Analogues
  作者：Galal E. H. Elgemeie、Ahmed H. H. Elghandour

  DOI：10.1246/bcsj.63.1230

  日期：1990.4

  Various benzopyrano[3,4-c]pyridine-4(3H)-thione derivatives and their oxo analogues were prepared by condensation of cyanothioacetamide or cyanoacetamide and salicylaldehyde with ketones or activated nitriles in the presence of ammonium acetate.

  通过将氰硫基乙酰胺或氰基乙酰胺与水杨醛在酮类或活化腈类存在下，与乙酸铵进行缩合反应，制备了多种苯并吡喃并[3,4-c]吡啶-4(3H)-硫酮衍生物及其氧化类似物。
• A New Pathway to 3-Hetaryl-2-oxo-2H-chromenes: On the Proposed Mechanisms for the Reaction of 3-Carbamoyl-2-iminochromenes with Dinucleophiles
  作者：Sergiy Kovalenko、Igor Bylov、Konstantyn Sytnik、Valentyn Chernykh、Yaroslav Bilokin

  DOI：10.3390/51001146

  日期：——

  The present account summarizes the author's studies to elucidate the mechanisms of the recently reported rearrangements resulting from inter- and/or intramolecular reactions of 2-imino-2H-chromene-3-carboxamides with different dinucleophiles.

  本报告总结了作者的研究，以阐明最近报道的由 2-亚氨基-2H-色烯-3-甲酰胺与不同双亲核试剂的分子间和/或分子内反应引起的重排机制。
• Reaction of 2-imino-2<i>H</i>-chromene-3-carboxamide with some phosphorus esters: Synthesis of some novel chromenes containing phosphorus heterocycles and phosphonate groups and their antioxidant and cytotoxicity properties
  作者：Tarik E. Ali、Mohammed A. Assiri、Hafez M. El-Shaaer、Mohamed M. Hassan、Ahmed M. Fouda、Noha M. Hassanin

  DOI：10.1080/00397911.2019.1652323

  日期：——

  phosphonate 6 have been obtained. In addition, some novel types of chromene fused with phosphorus heterocycles such as chromeno[4,3-c][1,2]azaphospholes 5 and 7, chromeno[2,3-d][1,3,2]diazaphosphinine 8 and 1,2-oxaphosphinino[3,4-c]pyridine 10 have been synthesized. The methodology depended on treatment of 2-imino-2H-chromene-3-carboxamide (1) with some phosphorus esters. The synthesized compounds were

  摘要 获得了新型的色烯基α-氨基膦酸4和二烷基色烯基膦酸酯6。此外，一些新型色烯与磷杂环稠合，如色烯[4,3-c][1,2]氮杂磷5和7、色烯[2,3-d][1,3,2]二氮杂膦8和1,2-oxaphosphinino [3,4-c] 吡啶 10 已被合成。该方法取决于用一些磷酯处理 2-亚氨基-2H-色烯-3-甲酰胺 (1)。对合成的化合物进行抗氧化和细胞毒活性评估。在合成的化合物中，与作为标准抗氧化剂的抗坏血酸相比，化合物 5 表现出最大的抗氧化活性，IC50 = 2.8 μg/mL。此外，化合物 5 对四种癌细胞系具有显着的细胞毒性作用。其 IC50 值介于 4.96 和 7 之间。与阿霉素相比为 44 μg/mL（IC50 = 0.426–0.493 μg/mL）。图形概要
• Regioselective cyclization reaction of 2-imino-2H-chromene-3-carboxamide with triethyl phosphonoacetate; a combined spectral and computational studies
  作者：Ibrahim A. Shaaban、Tarik E. Ali、Mohammed A. Assiri、Ahmed M. Fouda、Somaya M. Eledfawy、Noha M. Hassanin

  DOI：10.1016/j.molstruc.2019.126935

  日期：2020.1

  cyclization reaction of 2-imino-2H-chromene-3-carboxamide with triethyl phosphonoacetate was investigated by means of quantum mechanical calculation combined with infrared and NMR spectral analysis. Density functional theory (DFT) using B3LYP method at 6-31G(d,p) and 6-311++G(d,p) basis sets were used. Two possible pathways for this reaction were explored which resulted in the formation of two regioisomeric

  摘要 采用量子力学计算结合红外光谱和核磁共振光谱分析，研究了2-亚氨基-2H-色烯-3-甲酰胺与膦酰基乙酸三乙酯环化反应的区域选择性。密度泛函理论 (DFT) 使用 B3LYP 方法在 6-31G(d,p) 和 6-311++G(d,p) 基组中使用。探索了该反应的两种可能途径，导致形成具有不同环骨架的两种区域异构产物；苯并恶磷并 [3,4-c] 吡啶 (BOPP) 和色基 [3,4-c] 氮杂膦 (CAP)。最初，预测两种产品 (BOPP/CAP) 的互变异构稳定性有利于羟基-酮互变异构结构 (S-3/S-6)。还使用 GIAO-B3LYP/6-311++G(d, p) 通过 PCM 方法模拟的 DMSO 溶剂中的计算。计算结果表明 BOPP 区域异构体 (S-3) 的能量差为 9.44 kcal/mol。在计算出的频率和化学位移的帮助下，观察到的红外波段和 NMR 共振被可靠地分配，并且实现了与
• Synthesis and antimicrobial evaluation of 3-(4-arylthieno[2,3-<i>d</i>]pyrimidin-2-yl)- 2<i>H</i>-chromen-2-ones
  作者：Sergiy V. Vlasov、Sergiy M. Kovalenko、Pavlo E. Shynkarenko、Konstantin Yu. Krolenko、Vitaliy S. Vlasov

  DOI：10.1515/hc-2018-0013

  日期：2018.8.28

  Abstract Syntheses of 3-(4-arylthieno[2,3-d]pyrimidin-2-yl)-2H-chromen-2-ones 5 by the reaction of 2-iminocoumarin-3-carboxamides 1 with (2-aminothiophen-3-yl)(aryl)methanones 2 and by the alternative Suzuki coupling of 4-chlorothieno[2,3-d]pyrimidin-2-yl-2H-chromen-2-one 7 with arylboronic acids were developed. Compound 5d showed higher antimicrobial activity against Staphylococcus aureus than the

  摘要 2-亚氨基香豆素-3-甲酰胺1与(2-氨基噻吩-3)反应合成3-(4-芳基噻吩并[2,3-d]嘧啶-2-基)-2H-色烯-2-酮5 -yl)(aryl)methanones 2 和 4-chlorothieno[2,3-d]pyrimidin-2-yl-2H-chromen-2-one 7 与芳基硼酸的交替 Suzuki 偶联被开发出来。化合物 5d 对金黄色葡萄球菌的抗菌活性高于参考药物链霉素。