2-amino-4-oxo-4H-1-benzopyran-3-carbonitrile | 58778-37-3

• 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-amino-4-oxo-4H-1-benzopyran-3-carbonitrile
• 英文别名: 2-amino-4-oxo-4H-chromene-3-carbonitrile；2-amino-4-oxo-4H-chromene-3-carbonitrile；2-amino-3-cyano-chromone；2-amino-4-oxochromene-3-carbonitrile
• CAS: 58778-37-3
• 化学式: C₁₀H₆N₂O₂
• 分子量: 186.17
• InChiKey: HFGSYQXNEXRWDM-UHFFFAOYSA-N

物化性质

• 熔点：
  308-310 °C (decomp)(Solv: dichloromethane (75-09-2); ethyl ether (60-29-7))
• 沸点：
  359.3±42.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-oxo-4H-1-benzopyran-3-carbonitrile 以 吡啶 、 乙醇 为溶剂， 反应 0.67h， 生成 ethyl 4,5-dioxo-3H-<1>benzopyrano<2,3-d>pyrimidine-2-carboxylate
  参考文献：
  名称：

  Bevan, Peter S.; Ellis, Gwynn P.; Hudson, Henrietta V., Journal of the Chemical Society. Perkin transactions I, 1986, p. 1643 - 1650

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-3-甲酰色酮 在 DMAD 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.0h， 生成 2-amino-4-oxo-4H-1-benzopyran-3-carbonitrile
  参考文献：
  名称：

  Ghosh, Chandra Kanta; Ghosh, Chandreyi; Patra, Amarendra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 4, p. 387 - 390

  摘要：

  DOI：

文献信息

• Synthesis of Functionalized<i>H</i>-[1]Benzopyrano[2,3-<i>b</i>]pyridines by the<i>Friedländer</i>Approach: Antimycobacterial and Antimicrobial Profile
  作者：Dhaval D. Haveliwala、Nimesh R. Kamdar、Prashant T. Mistry、Saurabh K. Patel

  DOI：10.1002/hlca.201200121

  日期：2013.5

  A series of functionalized H‐[1]benzopyrano[2,3‐b]pyridine derivatives were synthesized by the Friedländer reaction of 2‐amino‐4‐oxo‐4H‐chromene‐3‐carbonitriles 1 with malononitrile, ethyl cyanoacetate, or acetophenone (Scheme). The synthesized compounds 2–4 were screened for their in vitro activity against antitubercular, antibacterial, and antifungal species (Fig., Table). Among the synthesized compounds

  通过2-氨基-4-氧代-4 H-色烯-3-腈1的Friedländer反应与丙二腈，氰基乙酸乙酯或苯丙氨酸的Friedländer反应合成了一系列功能化的H- [1]苯并吡喃并[2,3- b ]吡啶衍生物。苯乙酮（Scheme）。筛选了合成的化合物2 – 4对抗结核，抗菌和抗真菌物种的体外活性（图，表）。在合成的化合物中，3c和4f的活性最高，对结核分枝杆菌H 37的抑制率为99％Rv，而化合物2f，3f和4d分别显示69％，63％和61％的抑制作用。4-氨基-7,9-二溴-1,5-二氢-2,5-二氧代2 H-铬色[2,3 - b ]吡啶-3-腈（3b）对大肠杆菌具有最强的抗菌活性大肠杆菌和铜绿假单胞菌。几种chromeno [2,3- b ]吡啶衍生物对金黄色葡萄球菌和白色念珠菌具有相同或更高的效力。
• Substituted 2-amino chromones and process for the preparation thereof
  申请人：Warner-Lambert Company

  公开号：US03932466A1

  公开（公告）日：1976-01-13

  This invention relates to substituted 2-amino chromones of the general structure I: ##SPC1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 may be hydrogen, hydroxy, lower alkyl or lower alkoxy of 1-6 carbon atoms, halogen such as chloro or bromo, or aryl such as phenyl, and X may be cyano or carboxamido. Two novel procedures for preparing substituted 2-amino chromones having the Formula I, starting with salicylic acid or substituted salicylic acid, are described. The compounds of this invention are active in the prevention of allergic and asthmatic reactions in mammals.

  本发明涉及一般结构I的取代2-氨基香豆素：##SPC1## 其中R.sub.1、R.sub.2、R.sub.3和R.sub.4可以是氢、羟基、1-6个碳原子的低烷基或低烷氧基、氯或溴等卤素或苯基，X可以是氰基或羧酰胺基。本文描述了两种用水杨酸或取代水杨酸为起始物制备具有式I的取代2-氨基香豆素的新方法。本发明化合物在预防哺乳动物过敏和哮喘反应方面具有活性。
• Synthesis of novel thiopyrimidines: an investigation of anti-tubercular and antimicrobial activity
  作者：Dhaval D. Haveliwala、Nimesh R. Kamdar、Prashant T. Mistry、Saurabh K. Patel

  DOI：10.1080/17415993.2010.523894

  日期：2011.10.1

  A variety of novel sulfur-containing tricyclic pyrimidine derivatives have been synthesized via the reaction of 2-amino-4-oxo-4H-chromene-3-carbonitriles 3(a-f) with different reagents and characterized by IR, H-1 NMR, C-13 NMR, mass spectrometry and elemental analysis. The anti-tubercular and antimicrobial activities of the synthesized compounds were investigated.[GRAPHICS].
• Chromone-Fused Cytosine Analogues: Synthesis, Biological Activity, and Structure–Activity Relationship
  作者：Dhaval D. Haveliwala、Nimesh R. Kamdar、Prashant T. Mistry、Saurabh K. Patel

  DOI：10.1080/15257770.2013.873128

  日期：2014.2

  The preparation of a series of novel chromone-fused cytosine analogues, i.e., chromeno[2,3-d]pyrimidines has been carried out from substituted 2-amino-4-oxo-4H-chromene-3-carbonitriles with urea, thiourea, and guanidine under different reaction conditions. These chromone-fused cytosine analogues were evaluated for their in vitro activity against Mycobacterium tuberculosis H(37)Rv strain and different microbial pathogenic strains in cell culture for their structure-activity relationships, respectively. Among the synthesized compounds, 2d, 3a, and 4e showed better results against Mycobacterium tuberculosis H(37)Rv. The compounds 2a, 2b, and 3a showed potential antibacterial activity against E. coli and P. aeruginosa, while the majority of compounds were found to be active against S. aureus as compared to ampicillin. The synthesized cytosine analogues having an imine (-CNH) have been less sensitive to the bacterial and fungal strains but have a more beneficial effect on Mycobacterium tuberculosis H(37)Rv.
• Reactivity of 3-formyl- and 3-cyanothiochromones toward some N- and C-nucleophiles. Novel synthesis of 3-substituted 2-aminothiochromones
  作者：Vyacheslav Ya. Sosnovskikh、Dmitri V. Sevenard、Vladimir S. Moshkin、Viktor O. Iaroshenko、Peter Langer

  DOI：10.1016/j.tet.2010.06.066

  日期：2010.9

  The reactions of 3-formylthiochromone with o-phenylenediamines, o-aminobenzenethiol, and indoles proceeded at the aldehyde group to give 3-(benzimidazol-2-yl)thiochromone, 3-(benzothiazol-2-yl) thiochromone. and 3-di(indol-3-yl)methylthiochromones, respectively. 3-Formyl- and 3-cyanothiochromones react with primary aromatic amines and phenylhydrazine to give the corresponding anils and phenylhydrazones of 3-formyl- and 2-amino-3-formylthiochromones. The reaction of 3-cyanochromones with o-phenylenediamines gave 2-amino-3-[(2-aminophenyl)iminomethyl]-4H-chromen-4-ones. (C) 2010 Published by Elsevier Ltd.