Mild and Facile Cleavage of 2-Cyanoethyl Ester Using Sodium Sulfide or Tetrabutylammonium Fluoride. Synthesis of 1, 4-Dihydropyridine Monocarboxylic Acids and Unsymmetrical 1, 4-Dihydropyridine Dicarboxylates
Mild and Facile Cleavage of 2-Cyanoethyl Ester Using Sodium Sulfide or Tetrabutylammonium Fluoride. Synthesis of 1, 4-Dihydropyridine Monocarboxylic Acids and Unsymmetrical 1, 4-Dihydropyridine Dicarboxylates
复制标题
使用硫化钠或四丁基氟化铵温和且轻松地裂解 2-氰乙基酯。
DOI：
10.1248/cpb.42.1579
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发表时间：
1994
影响因子：
1.7
通讯作者：
Y. Kita
中科院分区：
文献类型：
--
作者：
T. Ogawa;K. Hatayama;H. Maeda;Y. Kita
通过Hantzsch反应合成了几个3-(2-氰乙基)-1，4-二氢吡啶羧酸酯(16)。用弱碱如硫化钠或四丁基氟化铵在室温下处理这些羧酸盐，以良好的产率顺利地得到相应的1，4-二氢吡啶单羧酸(18)。将一元羧酸18n和18o分别与2-硝氧基丙醇或N-(2-羟乙基)烟酰胺对甲苯磺酸盐酯化，得到选择性冠状动脉扩张剂CD-349(5)和CD-832(6)。
Several 3-(2-cyanoethyl)-1, 4-dihydropyridine carboxylates (16) were prepared in moderate to good yields by means of the Hantzsch reaction. Treatment of these carboxylates with a weak base such as sodium sulfide or tetrabutylammonium fluoride at room temperature afforded smoothly the corresponding 1, 4-dihydropyridine monocarboxylic acids (18) in good yields. The monocarboxylic acids 18n and 18o were esterified with 2-nitrooxypropanol or N-(2-hydroxyethyl)nicotinamide p-toluenesulfonic acid salt to afford the selective coronary vasodilators CD-349 (5) and CD-832 (6), respectively.