3-(1-methoxy-but-3-enyl)-1H-quinoline-2-thione | 1620211-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(1-methoxy-but-3-enyl)-1H-quinoline-2-thione
• CAS: 1620211-86-0
• 化学式: C₁₄H₁₅NOS
• 分子量: 245.345
• InChiKey: AHQGKBKJAODQSY-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  3-(1-methoxy-but-3-enyl)-1H-quinoline-2-thione 在 碘 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以80%的产率得到2-iodomethyl-4-methoxy-4H-2,3-dihydrothiopyrano[2,3-b]quinoline
  参考文献：
  名称：

  I2-catalyzed base-free cyclization of 3-homoallylquinoline-2-thiones: facile synthesis of tetracyclic, furothiopyrano[2,3-b]quinolines

  摘要：

  I-2-catalyzed base-free reactions of 3-homoallylquinoline-2-thiones have been described for the synthesis of tetracyclic quinolines, tetrahydrofuro [2',4':4,6]thiopyrano[2,3-Nquinolines in excellent yields. Similarly, I2-catalyzed reactions could proceed to tricyclic quinolines from hydroxyl group protected 3-homoallylquinoline-2-thiones. However, deprotection of group in tricyclic quinoline with HI again transformed into tetracyclic quinoline. The sulfonium salt intermediate has been proposed to explain these reactions. (C) Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.041
• 作为产物：
  描述：

  2-Chloro-3-(1-methoxybut-3-enyl)quinoline 在 sodium sulfide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以88%的产率得到3-(1-methoxy-but-3-enyl)-1H-quinoline-2-thione
  参考文献：
  名称：

  I2-catalyzed base-free cyclization of 3-homoallylquinoline-2-thiones: facile synthesis of tetracyclic, furothiopyrano[2,3-b]quinolines

  摘要：

  I-2-catalyzed base-free reactions of 3-homoallylquinoline-2-thiones have been described for the synthesis of tetracyclic quinolines, tetrahydrofuro [2',4':4,6]thiopyrano[2,3-Nquinolines in excellent yields. Similarly, I2-catalyzed reactions could proceed to tricyclic quinolines from hydroxyl group protected 3-homoallylquinoline-2-thiones. However, deprotection of group in tricyclic quinoline with HI again transformed into tetracyclic quinoline. The sulfonium salt intermediate has been proposed to explain these reactions. (C) Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.041