2-(2-fluorophenyl)-4H-pyrido[3,2-e][1,3]oxazin-4-one | 1446357-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-fluorophenyl)-4H-pyrido[3,2-e][1,3]oxazin-4-one
• 英文别名: 2-(2-Fluorophenyl)pyrido[3,2-e][1,3]oxazin-4-one
• CAS: 1446357-55-6
• 化学式: C₁₃H₇FN₂O₂
• 分子量: 242.209
• InChiKey: PJHLHFBGBVVZIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  sodium (2-bromonicotinoyl)(2-fluorobenzoyl)amide 以 乙腈 为溶剂， 反应 0.25h， 以76%的产率得到2-(2-fluorophenyl)-4H-pyrido[3,2-e][1,3]oxazin-4-one
  参考文献：
  名称：

  Expeditive Access to 2-Substituted 4H-Pyrido[1,3]oxazin-4-ones via an Intramolecular O-Arylation

  摘要：

  Unreported 2-substituted 4H-pyrido[e][1,3]oxazin-4-ones are synthesized via an unprecedented intramolecular O-arylation of N-aroyl- and N-heteroaroyl-(iso)nicotinamides under microwave irradiations, in good to excellent yields. The broad applicability was demonstrated by 24 examples with a variety of substituents at the 2-position of the final compounds and 3 possible positions for the nitrogen atom of the pyridine ring. In addition, transformation of one of these compounds into 2-hydroxypyridyl-substituted 1,2,4-triazole and 1,2,4-oxazinone was realized. This approach opens a rapid access to a new bicyclic heteroaromatic chemical series with high potential in medicinal chemistry.

  DOI：

  10.1021/ol401516e

文献信息

• USE OF FUSED HETEROCYCLIC COMPOUNDS AS SCCE INHIBITORS FOR THE TREATMENT OF SKIN CONDITIONS OR CANCER
  申请人：Arexis AB

  公开号：EP1631295A2

  公开（公告）日：2006-03-08
• [EN] USE OF HETEROCYCLIC COMPOUNDS AS SCCE INHIBITORS<br/>[FR] UTILISATION DE COMPOSES HETEROCYCLIQUES EN TANT QU'INHIBITEURS DE SCCE
  申请人：AREXIS AB

  公开号：WO2004108139A2

  公开（公告）日：2004-12-16

  The present invention relates to heterocyclic inhibitors of stratum corneum chymotryptic enzyme (SCCE). More particularly, the invention relates to the use of compounds with the formula (I) or (II) for treatment of certain diseases, in particular skin diseases such as pruirtus, as well as cancer such as ovarian cancer.
• Expeditive Access to 2-Substituted 4<i>H</i>-Pyrido[1,3]oxazin-4-ones <i>via</i> an Intramolecular O-Arylation
  作者：Franck Slowinski、Omar Ben Ayad、Ozge Ziyaret、Candice Botuha、Laetitia Le Falher、Kamel Aouane、Serge Thorimbert

  DOI：10.1021/ol401516e

  日期：2013.7.19

  Unreported 2-substituted 4H-pyrido[e][1,3]oxazin-4-ones are synthesized via an unprecedented intramolecular O-arylation of N-aroyl- and N-heteroaroyl-(iso)nicotinamides under microwave irradiations, in good to excellent yields. The broad applicability was demonstrated by 24 examples with a variety of substituents at the 2-position of the final compounds and 3 possible positions for the nitrogen atom of the pyridine ring. In addition, transformation of one of these compounds into 2-hydroxypyridyl-substituted 1,2,4-triazole and 1,2,4-oxazinone was realized. This approach opens a rapid access to a new bicyclic heteroaromatic chemical series with high potential in medicinal chemistry.