oxazolo[5,4-b]pyridine-2-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶唑并吡啶类
• 英文名称: oxazolo[5,4-b]pyridine-2-carbonitrile
• 英文别名: [1,3]oxazolo[5,4-b]pyridine-2-carbonitrile
• 化学式: C₇H₃N₃O
• 分子量: 145.12
• InChiKey: DFIOLFLPYZMXLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.71
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-氨基-2-羟基吡啶 以 二氯甲烷 、 氯苯 为溶剂， 反应 4.0h， 生成 oxazolo[5,4-b]pyridine-2-carbonitrile
  参考文献：
  名称：

  Ring transformations of 2-hydroxy-(4-chloro-5 H -1,2,3-dithiazol-5-ylideneamino)arenes

  摘要：

  The cyclisation reactions of 2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene-amino)phenol (5a), 3-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)pyridin-2-ol (5b) and 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)pyridin-3-ol (5c) are investigated. Thermolysis in hot PhCl (132 degrees C) or under solvent free conditions at ca. 200 degrees C gave benzo[d]oxazole-2-carbonitrile (4a), oxazolo[5,4-b]pyridine-2-carbonitrile (4b) and oxazolo[4,5-b]pyridine-2-carbonitrile (4c) in high yields, while treatment with either NaH in dry THF at 66 degrees C or with i-Pr2NEt in DCM at 20 degrees C gave benzo[b][1,2,3]clithiazolo[5,4-e][1,41 oxazine (6a), [1,2,3]dithiazolo[5,4-e]pyrido[2,3-b][1,4]oxazine (6b) and oxazolo[4,5-b]pyridine (4c), respectively. The transformation of benzoxazine 6a and the pyridoxazine 6b into the corresponding oxazoles 4a and 4b was also investigated, and tentative mechanistic pathways for these transformations are proposed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.046

文献信息

• Ring transformations of 2-hydroxy-(4-chloro-5 H -1,2,3-dithiazol-5-ylideneamino)arenes
  作者：Andreas S. Kalogirou、Sophia S. Michaelidou、Maria Koyioni、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2014.12.046

  日期：2015.9

  The cyclisation reactions of 2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene-amino)phenol (5a), 3-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)pyridin-2-ol (5b) and 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)pyridin-3-ol (5c) are investigated. Thermolysis in hot PhCl (132 degrees C) or under solvent free conditions at ca. 200 degrees C gave benzo[d]oxazole-2-carbonitrile (4a), oxazolo[5,4-b]pyridine-2-carbonitrile (4b) and oxazolo[4,5-b]pyridine-2-carbonitrile (4c) in high yields, while treatment with either NaH in dry THF at 66 degrees C or with i-Pr2NEt in DCM at 20 degrees C gave benzo[b][1,2,3]clithiazolo[5,4-e][1,41 oxazine (6a), [1,2,3]dithiazolo[5,4-e]pyrido[2,3-b][1,4]oxazine (6b) and oxazolo[4,5-b]pyridine (4c), respectively. The transformation of benzoxazine 6a and the pyridoxazine 6b into the corresponding oxazoles 4a and 4b was also investigated, and tentative mechanistic pathways for these transformations are proposed. (C) 2014 Elsevier Ltd. All rights reserved.