6-methylchromone-3-carboxamide | 1447230-29-6

• 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: 6-methylchromone-3-carboxamide
• 英文别名: 6-Methylchromone-3-carboxamide；6-methyl-4-oxochromene-3-carboxamide
• CAS: 1447230-29-6
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: OHSOYRBLMKFUKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methylchromone-3-carboxamide 、 氰乙酰胺 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以74%的产率得到2-amino-5-(2-hydroxy-5-methylbenzoyl)-6-oxo-1,6-dihydropyridine-3-carboxamide
  参考文献：
  名称：

  Synthesis of 2-amino-6-oxo-5-salicyloyl-1,6-dihydropyridine- 3-carboxamides from 3-carbamoylchromones and cyanoacetamides

  摘要：

  3-Carbamoylchromones reacted with cyanoacetamides in the presence of sodium ethoxide in refluxing ethanol, forming 2-amino-5-aroyl-6-oxo-1,6-dihydropyridine-3-carboxamides in 50-88% yields.

  DOI：

  10.1007/s10593-015-1758-6

文献信息

• Reactions of chromone-3-carboxylic acid and chromone-3-carboxamides with cyanoacetic acid hydrazide
  作者：Mikhail Yu. Kornev、Vladimir S. Moshkin、Oleg S. Eltsov、Vyacheslav Ya. Sosnovskikh

  DOI：10.1016/j.mencom.2016.01.028

  日期：2016.1

  Chromone and chromone-3-carboxylic acid react with cyanoacetic acid hydrazide in the presence of NaOEt in boiling ethanol to form 6-(2-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridin-3(2H)-one (58–62% yields), whereas reaction between chromone-3-carboxamides and cyanoacetic acid hydrazide under the same conditions affords 1-amino-2,5-dioxo-2,5-dihydro-1H-chromeno[4,3-b]pyridine-3-carbonitriles (50–67% yields)

  在NaOEt存在下，在沸腾的乙醇中，色酮和色酮3-羧酸与氰基乙酸酰肼反应形成6-（2-羟苯基）-1H-吡唑并[3,4-b]吡啶-3（2H）-one（ 58–62％的产率），而色酮3-羧酰胺与氰基乙酸酰肼在相同条件下反应，可得到1-氨基-2,5-二氧代-2,5-二氢-1H-铬基[4,3-b]吡啶-3-甲腈（50-67％的收率）。
• Studies on the chemical reactivity of 1H-benzimidazol-2-ylacetonitrile towards some 3-substituted chromones: synthesis of some novel pyrido[1,2-a]benzimidazoles
  作者：Magdy A. Ibrahim

  DOI：10.1016/j.tet.2013.06.011

  日期：2013.8

  A simple and convenient synthesis of a novel series of pyrido[1,2-a]benzimidazoles was efficiently achieved from the condensation reactions of 1H-benzimidazol-2-ylacetonitrile (1) with some 3-substituted chromones, chromone-3-carboxylic acids, chromone-3-carboxamides, ethyl chromone-3-carboxylates and chromone-3-carbonitriles. Reaction of compound 1 with 2-aminochromone-3-carboxaldehydes produced

  1 H-苯并咪唑-2-基乙腈（1）与某些3-取代的色酮，色酮-3-羧基的缩合反应可有效地简单，方便地合成一系列新的吡啶并[1,2- a ]苯并咪唑类化合物酸，苯甲酸酯-3-甲酰胺，苯甲酸酯-3-羧酸盐和苯甲酸酯-3-甲腈。化合物1与2-氨基色酮-3-羧醛的反应产生2-氨基-3-（1H-苯并咪唑-2-基）铬诺[2，3- b ]吡啶。还讨论了反应机理和光谱数据。
• Reactions of chromone-3-carboxamides with 2-cyanothioacetamides
  作者：Mikhail Yu. Kornev、Denis S. Tishin、Vyacheslav Ya. Sosnovskikh

  DOI：10.1016/j.mencom.2019.01.022

  日期：2019.1

  Chromone-3-carboxamides react with cyanothioacetamide in the presence of NaOEt in boiling ethanol to form 5-oxo-2-thioxo-1,5-dihydro-2H-chromeno[4,3-b]pyridine-3-carbo-nitrites (67-87% yields), whereas their reaction with N-methyl-cyanothioacetamide and a catalytic amount of Et3N in boiling ethanol affords 5-cyano-2-(2-hydroxyphenyl)-1-methyl-6-thioxo-1,6-dihydropyridine-3-carboxamides in 57-73% yields.