The Synthesis, Structure and Properties of N-Acetylated Derivatives of Ethyl 3-Amino-1H-pyrazole-4-carboxylate

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概要

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• Ethyl 3-amino-1H-pyrazole-4-carboxylate (1) was yielded through total synthesis and reacted with acetic anhydride to give the acetylated products 2-6. Compounds 1-6 were studied with HPLC, X-ray, FT-IR, ^1H-NMR, ^<13>C-NMR and MS. Acetylation was carried out in solvents of various polarity, namely; chloroform; dioxane; DMF; acetic anhydride, at room temperature and at boiling points; and in the presence and absence of DMAP. The acetylated products are mainly nitrogen atoms in the ring. The position of the ring proton in the solution was based on NOESY; multinuclear HMBC, HSQC spectra and calculations. For equivalent amounts (1-1.5mol) of acetic anhydride at room temperature two products of monoacetylation are produced in the ring: 2 and 3, ca.2:1 and at the same time only small amount of the third product of monoacetylated, 5 in DMF, as well the product diacetylated, 4. The greatest amount of the product 4 is produced during the reaction with chloroform. However, in this solvent and in dioxane no product 5 is produced. Compound 2 is, largely, formed in dimethylformamide, in the presence DMAP, 0.2 eq. In the presence of this catalytic base, for the first hour, there is a mixture 2 and 3 to the ratio ca. 95:5. With 8 eq of Ac_2O at reflux, after another hour, the compounds 3, 4 and 6 appear about equal amounts. After a longer time, the compound, which appears most in this mixture is triacetylated derivative 6. The structural and spectroscopic characteristics of compounds 1-6 have been given and the methods for their preparation have been provided.

• 公益社団法人日本薬学会の論文
• 2007-05-01

著者

• Rzeszotarska B

  Institute Of Chemistry University Of Opole

• Kusakiewicz-dawid Anna

  Institute Of Chemisty University Of Opole

• MASIUKIEWICZ Elzbieta

  Institute of Chemisty, University of Opole

• RZESZOTARSKA Barbara

  Institute of Chemisty, University of Opole

• DYBALA Izabela

  Faculty of Chemistry, Maria Curie-Sklodowska University

• KOZIOL Anna

  Faculty of Chemistry, Maria Curie-Sklodowska University

• BRODA Malgorzata

  Institute of Chemisty, University of Opole

• Dybala Izabela

  Faculty Of Chemistry Maria Curie-sklodowska University

• Broda Malgorzata

  Institute Of Chemisty University Of Opole

• Masiukiewicz E

  Institute Of Chemisty University Of Opole

• Koziol Anna

  Faculty Of Chemistry Maria Curie-sklodowska University

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