3-(4-chlorobenzoylamino)methylthio-1H-indole | 1060654-21-8

• 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: 3-(4-chlorobenzoylamino)methylthio-1H-indole
• 英文别名: 4-chloro-N-(1H-indol-3-ylsulfanylmethyl)benzamide
• CAS: 1060654-21-8
• 化学式: C₁₆H₁₃ClN₂OS
• 分子量: 316.811
• InChiKey: ONVUCCQJHNDKDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-chlorobenzoylamino)methylthio-1H-indole 在 三氟甲磺酸 作用下， 以84%的产率得到2-(4-chlorobenzoylaminomethylthio)-1H-indole
  参考文献：
  名称：

  An expeditious synthesis for γ-carboline analogue 4-aryl-1,3-thiazino[6,5-b]indole derivatives via the trifluoromethanesulfonic acid-promoted isomerization of 3-amidomethylthioindole intermediates to 2-indolyl sulfides

  摘要：

  A highly efficient trifluoromethanesulfonic acid-mediated rearrangement of the benzoylaminomethylthio group of 3-benzoylaminomethylthioindoles (7a-e) to position 2 of the indole ring was developed. Thus, 2-benzoylaminomethylthioindoles (9a-e) were obtained in good yields and were involved as key intermediates in the synthesis of the new gamma-carboline analogue ring system: 2,9-dihydro-4-aryl-1,3-thiazino[6,5-b]indole derivatives (11a-e). The target thiazinoindoles (11a-e) were prepared via 2-thiobenzoylaminomethylindoles (10a-e) in modified Bischler-Napieralski reactions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.099
• 作为产物：
  描述：

  3-巯基吲哚 、 (4-chlorobenzoylaminomethyl)triethylammonium chloride 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以94%的产率得到3-(4-chlorobenzoylamino)methylthio-1H-indole
  参考文献：
  名称：

  Synthesis of 4-thiaharmalan analogue 4-aryl-1,3-thiazino[5,6-b]indole derivatives by prevention of rearrangements to position two of the indole moiety

  摘要：

  An efficient and selective non-acidic protocol has been developed for the synthesis of derivatives of a new ring system: 4-aryl-1,3-thiazino[5,6-b]indole, a 4-thiaharmalan analogue. The convenient amidomethylation of indole-3-thiol (5) afforded 3-beilzoylaminomethyithio-1H-indole (7a). with orthoamidomethylated 2-benzoylamino-methyl-3-benzoylaminomethylthio-1H-indole (8) as side product. Following the Bischler-Napieralski reaction of 7a the rearranged 2-benzoylaminomethylthio-1H-indole 11 could be isolated. In order to prevent such rearrangements the target thiazinoindoles were prepared via 3-thiobenzoylanlinomethylthioindole (13) via a modified Bischler-Napieralski reaction. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.014

文献信息

• Synthesis of 4-thiaharmalan analogue 4-aryl-1,3-thiazino[5,6-b]indole derivatives by prevention of rearrangements to position two of the indole moiety
  作者：Péter Csomós、Lajos Fodor、Gábor Bernáth、Antal Csámpai、Pál Sohár

  DOI：10.1016/j.tet.2008.07.014

  日期：2008.9

  An efficient and selective non-acidic protocol has been developed for the synthesis of derivatives of a new ring system: 4-aryl-1,3-thiazino[5,6-b]indole, a 4-thiaharmalan analogue. The convenient amidomethylation of indole-3-thiol (5) afforded 3-beilzoylaminomethyithio-1H-indole (7a). with orthoamidomethylated 2-benzoylamino-methyl-3-benzoylaminomethylthio-1H-indole (8) as side product. Following the Bischler-Napieralski reaction of 7a the rearranged 2-benzoylaminomethylthio-1H-indole 11 could be isolated. In order to prevent such rearrangements the target thiazinoindoles were prepared via 3-thiobenzoylanlinomethylthioindole (13) via a modified Bischler-Napieralski reaction. (c) 2008 Elsevier Ltd. All rights reserved.
• An expeditious synthesis for γ-carboline analogue 4-aryl-1,3-thiazino[6,5-b]indole derivatives via the trifluoromethanesulfonic acid-promoted isomerization of 3-amidomethylthioindole intermediates to 2-indolyl sulfides
  作者：Péter Csomós、Lajos Fodor、Gábor Bernáth、Antal Csámpai、Pál Sohár

  DOI：10.1016/j.tet.2008.11.099

  日期：2009.2

  A highly efficient trifluoromethanesulfonic acid-mediated rearrangement of the benzoylaminomethylthio group of 3-benzoylaminomethylthioindoles (7a-e) to position 2 of the indole ring was developed. Thus, 2-benzoylaminomethylthioindoles (9a-e) were obtained in good yields and were involved as key intermediates in the synthesis of the new gamma-carboline analogue ring system: 2,9-dihydro-4-aryl-1,3-thiazino[6,5-b]indole derivatives (11a-e). The target thiazinoindoles (11a-e) were prepared via 2-thiobenzoylaminomethylindoles (10a-e) in modified Bischler-Napieralski reactions. (C) 2008 Elsevier Ltd. All rights reserved.