methyl 3-isopropyl-4-(methylthio)-6-oxo-1,6-dihydropyridine-2-carboxylate | 1187027-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 3-isopropyl-4-(methylthio)-6-oxo-1,6-dihydropyridine-2-carboxylate
• CAS: 1187027-66-2
• 化学式: C₁₁H₁₅NO₃S
• 分子量: 241.311
• InChiKey: MGQQNTNAGUVHOA-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  methyl 3-isopropyl-4-(methylthio)-6-oxo-1,6-dihydropyridine-2-carboxylate 在 三乙基硅烷 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以83%的产率得到methyl 3-isopropyl-6-oxo-1,6-dihydropyridine-2-carboxylate
  参考文献：
  名称：

  An annulation method for the synthesis of alkyl-substituted 6-carbomethoxy-2-pyridones

  摘要：

  A protocol for the synthesis of 5-alkyl and 3,5-dialkyl-6-carbomethoxy-2-pyridones was devised. Key steps include a Mannich reaction, acylation of a tosylamine, and a PPh3/TiCl4-promoted intramolecular Reformatsky-type reaction with a thioester as the electrophile. The latter process typically afforded a vinylogous thiocarbamate via elimination of water rather than the Dieckmann-type product which would have resulted from elimination of the thiol. However, the Dieckmann-type ketone product was obtained in one instance. Subsequent elimination of the tosyl group and desulfurization completed the pyridone synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.006
• 作为产物：
  描述：

  methyl 3-isopropyl-4-(methylthio)-6-oxo-1-tosyl-1,2,3,6-tetrahydropyridine-2-carboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以96%的产率得到methyl 3-isopropyl-4-(methylthio)-6-oxo-1,6-dihydropyridine-2-carboxylate
  参考文献：
  名称：

  An annulation method for the synthesis of alkyl-substituted 6-carbomethoxy-2-pyridones

  摘要：

  A protocol for the synthesis of 5-alkyl and 3,5-dialkyl-6-carbomethoxy-2-pyridones was devised. Key steps include a Mannich reaction, acylation of a tosylamine, and a PPh3/TiCl4-promoted intramolecular Reformatsky-type reaction with a thioester as the electrophile. The latter process typically afforded a vinylogous thiocarbamate via elimination of water rather than the Dieckmann-type product which would have resulted from elimination of the thiol. However, the Dieckmann-type ketone product was obtained in one instance. Subsequent elimination of the tosyl group and desulfurization completed the pyridone synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.006