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1,3-二甲基-5-甲氧基-2,3-二氢-2-氧-1H-吲哚-3-丙烯酸甲酯的制备

Preparation of Methyl 1,3-Dimethyl-5-methoxy-2,3-dihydro-2-oxy-1H-indole-3-acrylate
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摘要 1,3-二甲基-5-甲氧基-2,3-二氢-2-氧-1H-吲哚-3-丙烯酸甲酯(1)可在Pd/C催化下加氢还原碳-碳双键,再经酯基水解成酸、Curtius重排及环合反应等转化为毒扁豆碱(physostigmine)和eserethole的合成前体。1的合成方法未见报道。 Methyl 1,3-dimethyl-5-methoxy-2,3-dihydro-2-oxy-1H-indole-3-acrylate was prepared by the addition-elimination reaction of 1,3-dimethyl-5-methoxy-2,3-dihydro-2-oxy-1H-indole and methyl 3-(1-imidazolyl)acrylate in the presence of n-BuLi in a yield of 90%.
出处 《中国医药工业杂志》 CAS CSCD 北大核心 2010年第11期807-808,共2页 Chinese Journal of Pharmaceuticals
关键词 丙烯酸甲酯 加氢还原 吲哚 Curtius重排 制备 合成方法 碳-碳双键 methyl 1 3-dimethyl-5-methoxy-2 3-dihydro-2-oxy-1H-indole-3-acrylate intermediate physostigmine eserethole preparation
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参考文献5

  • 1Julian PL, Pikl J. Studies in the indole series. IV. The synthesis of d,l-eserethole [J]. JAm Chem Soc, 1935, 57 (3): 563-566.
  • 2Node M, Hao X J, Nishide K, et al. A formal asymmetric synthesis of calabar bean alkaloids [J]. Chem Pharm Bull, 1996, 44(4): 715-719.
  • 3Yamada S, Hino T, Ogawa K. The reductive cyclization of 1-methyl-3-aminoalkyloxindoles with lithium aluminum hydride [J]. Chem Pharm Bull, 1963, 11 (5):674-677.
  • 4Morales-Rios MS, Bucio MA, Joseph-Nathan P. Formal synthesis of (±)-physostigmine [J]. Tetrahedron, 1996, 52 (15) : 5339-5348.
  • 5Kashima C, Tajima T, Omote Y. The compounds related to 3-(1-imidazolyl)-2-alken-l-ones. Preparation and reactions [J]. JHeterocycl Chem, 1984, 21 (1): 171-175.

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