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
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- OGAWA Toshihisa
- Research Center, Taisho Pharmaceutical Co., Ltd.,
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- HATAYAMA Katsuo
- Research Center, Taisho Pharmaceutical Co., Ltd.,
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- MAEDA Hiroshi
- Faculty of Pharmaceutical Sciences, Osaka University
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- KITA Yasuyuki
- Faculty of Pharmaceutical Sciences, Osaka University
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Abstract
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.
Journal
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- Chemical & pharmaceutical bulletin
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Chemical & pharmaceutical bulletin 42 (8), 1579-1589, 1994-08-15
The Pharmaceutical Society of Japan
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Keywords
Details 詳細情報について
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- CRID
- 1571980077277972608
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- NII Article ID
- 110003631192
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- NII Book ID
- AA00602100
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- ISSN
- 00092363
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- Text Lang
- en
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- Data Source
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- CiNii Articles