The Synthetic Intermediate of Pyridoxine. II. The Thermal Cyclization of Ethyl α-Isocyanopropionate to 5-Ethoxy-4-methyloxazole

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概要

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• The thermal cyclization of ethyl α-isocyanopropionate (I) was performed to 5-ethoxy-4-methyloxazole (II) as an intermediate for the synthesis of pyridoxine. The similar reaction of several new alkyl esters of α-isocyanocarboxylic acid to the corresponding 5-alkoxy-4-substituted oxazole was also carried out. The reaction products of the thermal cyclization of I were investigated. When the cyclization was carried out at 180°C for 5 hr, the maximum yield of the main product, II, was 20%; unreacted I (30%), ethyl α-cyanopropionate(20%), and dimer of I (5%) were also obtained. The α-hydrogen of ethyl α-isocyanosuccinate (X) can be more easily removed than that of I, so X may be expected to be more readily converted to 5-ethoxy-4-ethoxycarbonylmethyloxazole (XI), which is also an intermediate of pyridoxine. The yield of XI from X did not exceed 30% because of the side reaction.

• 公益社団法人 日本化学会の論文

著者

• Yoshida Ryonosuke

  Central Research Laboratories, Ajinomoto Co., Inc.

• Maeda Itsutoshi

  Central Research Laboratories, Ajinomoto Co., Inc.

• Togo Kazushi

  Central Research Laboratories, Ajinomoto Co., Inc.

関連論文

• The Synthetic Intermediate of Pyridoxine. II. The Thermal Cyclization of Ethyl α-Isocyanopropionate to 5-Ethoxy-4-methyloxazole
• The Synthetic Intermediate of Pyridoxine. III. The Simple Synthesis of Ethyl N-Ethoxalylalaninate and Ethyl N-Formylalaninate

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