Synthesis, Structure and Properties of N-Acetylated Derivatives of Methyl 5-Amino-1H-[1,2,4]triazole-3-carboxylate

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概要

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• Methyl 5-amino-1H-[1,2,4]triazole-3-carboxylate hydrochloride (1) and free ester (2) were obtained and 2 was reacted with Ac_2O to give the acetylated products 3-6. Compounds 1-6 were studied using HPLC, GC-MS, FTIR and multinuclear NMR spectroscopy, including the cross-polarisation magic angle spinning (CPMAS) technique. The results of the acetylation of 2 were compared to those of the acetylation of 5-amino-1H-(1,2,4]triazole, and for 2 a significant decrease in the susceptibility to acetylation was found. The reaction of 2 with Ac_2O at 20 ℃, regardless of the amount and the concentration of the latter, including neat Ac_2O, proceeds fully regioselectively and leads to one product: methyl 1-acetyl-5-amino-1H-[1,2,4]triazole-3-carboxylate (3). In sharp contrast to 5-amino-1H-[1,2,4]triazole, neither an additional monoacetylated isomer, whether annular or exocyclic, nor any diacetylated derivative could be detected. The diacetylation of 2 requires the process to be carried out in neat boiling Ac_2O and, as in the case of 5-amino-1H-[1,2,4]triazole, gives two diacetylated isomers. These are methyl 1-acetyl-3-(acetylamino)-1H-[l,2,4]triazole-5-carboxylate (4) and 1-acetyl-5-(acetylamino)-1H-[1,2,4]triazole-3-carboxylate (5). Hypothetical pathways of their formation have been suggested. A mixture of 4 and 5 upon hydrolysis of the ring acetyl group gives the monoacetylated derivative methyl 5-(acetylamino)-1H-[1,2,4]triazole-3-carboxylate (6). The spectroscopic, structural and conformational characteristics of compounds 1-6 have been given and methods for their preparation have been provided.

• 公益社団法人日本薬学会の論文
• 2004-02-01

著者

• Kamienski Bohdan

  Institute Of Organic Chemistry Polish Academy Of Sciences

• Rzeszotarska B

  Institute Of Chemistry University Of Opole

• MASIUKIEWICZ Elzbieta

  Institute of Chemisty, University of Opole

• RZESZOTARSKA Barbara

  Institute of Chemisty, University of Opole

• DZYGtEL Anetta

  Institute of Chemistry, University of Opole

• CMOCH Piotr

  Institute of Organic Chemistry, Polish Academy of Sciences

• Cmoch Piotr

  Institute Of Organic Chemistry Polish Academy Of Sciences

• Dzygtel Anetta

  Institute Of Chemistry University Of Opole

• Masiukiewicz E

  Institute Of Chemisty University Of Opole

• Dzygiel Anetta

  Institute of Chemistry, University of Opole

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