5H-thiochromeno[2,3-b]pyridin-5-one | 5698-68-0

• 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: 5H-thiochromeno[2,3-b]pyridin-5-one
• 英文别名: 5H-[1]benzothiopyrano[2,3-b]pyridin-5-one；4-azathioxanthone；5H-[1]benzothiopyrano[2,3-b]pyridine-5-one；thiochromeno[2,3-b]pyridin-5-one；Thiochromeno[2,3-b]pyridin-5-on；Thiochromeno[2,3-b]pyridin-5-one
• CAS: 5698-68-0
• 化学式: C₁₂H₇NOS
• 分子量: 213.26
• InChiKey: VEOSCXKPFWPNIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5H-thiochromeno[2,3-b]pyridin-5-one 在 sodium tetrahydroborate 、 四氯化钛 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 5.5h， 生成 1,3-dimethyl-1-(10,10-dioxo-5H-[1]benzothiopyrano[2,3-b]pyridin-5-yl)urea
  参考文献：
  名称：

  胃抗分泌剂。1. 5H- [1]苯并吡喃并[2,3-b]吡啶-5-基脲和5H- [1]苯并噻喃并[2,3-b]吡啶-5-基脲的抗分泌和抗溃疡活性。

  摘要：

  DOI：

  10.1021/jm00140a004
• 作为产物：
  描述：

  (2-溴-5-甲氧基苯基)(2-氯吡啶-3-基)甲酮 在 sodiumsulfide nonahydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以88%的产率得到5H-thiochromeno[2,3-b]pyridin-5-one
  参考文献：
  名称：

  A Convenient Synthesis of 9H-Thioxanthen-9-ones and Their Aza-Analogues

  摘要：

  An efficient method for the preparation of 9H-thioxanthen-9-ones and their three aza-analogues has been developed. The reaction of (2-fluorophenyl)(2-halophenyl)methanones, derived from 1-bromo-2-fluorobenzenes and 2-halobenzaldehydes by an easy two-step sequence, with Na2S center dot 9H(2)O in DMF at 60 degrees C gives 9H-thioxanthen-9-ones. This procedure can be applied to the synthesis of 5H-[1]benzothiopyrano[2,3-b] (or [2,3-c])pyridin-5-ones or 10H-[1]benzothiopyrano[3,2-c]pyridin-10-ones starting from 2-, 3- or 4-chloropyridines, respectively.

  DOI：

  10.3987/com-13-12855

文献信息

• Functionalization of pyridyl ketones using deprotolithiation-in situ zincation
  作者：Madani Hedidi、William Erb、Frédéric Lassagne、Yury S. Halauko、Oleg A. Ivashkevich、Vadim E. Matulis、Thierry Roisnel、Ghenia Bentabed-Ababsa、Florence Mongin

  DOI：10.1039/c6ra11370b

  日期：——

  The metallation of aryl ketones was achieved by using LiTMP in the presence of ZnCl2·TMEDA, as evidenced by subsequent interception with iodine or by a palladium-catalysed cross-coupling reaction. One of the synthesized iodo ketones has been further elaborated to reach derivatives of biological interest.

  芳基酮的金属化是通过在ZnCl 2 ·TMEDA存在下使用LiTMP来实现的，随后通过碘的拦截或钯催化的交叉偶联反应证明了这一点。合成的碘代酮之一已被进一步精加工以达到具有生物学意义的衍生物。
• Palladium(II)-catalyzed direct annulation of 2-chloronicotinaldehyde with 2-bromothiophenol via novel C(formyl)-C(aryl) coupling strategy
  作者：Mayur I. Morja、Prakashsingh M. Chauhan、Kishor H. Chikhalia

  DOI：10.1007/s11164-021-04536-1

  日期：2021.11

  unprecedented method to the synthesis of 1-azathioxanthone derivatives has been developed by means of palladium-catalyzed C(formyl)-C(aryl) coupling followed by SNAr reaction. Optimization study was carried out through different catalyst, ligand, base and solvent. This approach displays various exclusive characteristics such as operational convenience, moderate to good isolated yields and decent functional

  通过钯催化的 C(甲酰基)-C(芳基)偶联，然后进行 SNAr 反应，开发了一种有效且前所未有的合成 1-硫杂蒽酮衍生物的方法。通过不同的催化剂、配体、碱和溶剂进行优化研究。这种方法显示了各种独特的特性，例如操作方便、中等至良好的分离产率和良好的官能团耐受性。 图形摘要
• Synthesis of 1-Azaxanthones and 1-Azathioxanthones by Yb(OTf)3/TfOH Co-Catalyzed Intramolecular Friedel-Crafts Reaction
  作者：Weike Su、Can Jin、Jie Li

  DOI：10.3987/com-10-12029

  日期：——

  Intramolecular Friedel-Crafts cyclization of phenoxypyridine acids (3a-3j) and phenythiopyridine acids (4a-4i) to form 1-azaxanthones (1a-1j) and 1-azathioxanthones (2a-2i), respectively, was efficiently promoted by Yb(OTf) 3 /TfOH as co-catalysts. And a number of substrates could be cyclized in moderate to good yields.

  Yb(OTf) 有效促进苯氧基吡啶酸 (3a-3j) 和苯硫代吡啶酸 (4a-4i) 的分子内 Friedel-Crafts 环化分别形成 1-氮杂蒽酮 (1a-1j) 和 1-氮杂噻吨酮 (2a-2i) ) 3 /TfOH 作为助催化剂。并且许多底物可以以中等至良好的产率进行环化。
• Nucleophilic addition to 2,3-pyridyne and synthesis of benzonaphthyridinones
  作者：Yuesi Fang、Richard C. Larock

  DOI：10.1016/j.tet.2012.02.002

  日期：2012.4

  A study of the nucleophilic addition of amines to 2,3-pyridyne has been carried out. 2-Aminopyridines have been generated exclusively. A series of benzonaphthyridinones have been synthesized by reacting 2,3-pyridyne and o-aminobenzoates. (C) 2012 Elsevier Ltd. All rights reserved.
• 382. Xanthones and thioxanthones. Part IV. The preparation and properties of 9-oxa-1-aza-anthrone and 9-thia-1-aza-anthrone
  作者：Frederick G. Mann、J. A. Reid

  DOI：10.1039/jr9520002057

  日期：——