Recyclization of Condensed Carbethoxypyrimidines Accompanied by Substitution of a Carbon Atom into the Heterocycle |
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Authors: | G G Danagulyan A D Mkrtchyan G A Panosyan |
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Institution: | (1) Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, Yerevan, 375094, Armenia;(2) Molecular Structure Research Center, National Academy of Sciences of the Republic of Armenia, Yerevan, 375014, Armenia |
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Abstract: | Condensation in ethanol of ethyl ethoxymethyleneacetoacetate with systems containing an amidine fragment (substituted 3-aminopyrazoles and 3-amino-1,2,4-triazole) gave 6-carbethoxy-7-methylpyrazolo1,5-a]pyrimidines. Addition of base to solutions of the obtained bicyclic carbethoxy derivatives in the course of several minutes caused rearrangement to 6-acetyl-7-hydroxypyrazolo1,5-a]pyrimidine and 6-acetyl-7-hydroxy-1,2,4-triazolo1,5-a]pyrimidine respectively. A more prolonged refluxing in 15% aqueous alcohol solution of base caused 6-carbethoxy-7-methyl-2-phenylpyrazolo1,5-a]pyrimidine and 6-acetyl-7-hydroxy-2-phenylpyrazolo1,5-a]pyrimidine to recyclize to 7-methylpyrazolo1,5-a]pyrimidine.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 569–576, April, 2005. |
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Keywords: | pyrazolo[1 5-a]pyrimidine 1 2 4-triazolo[1 5-a]pyrimidine rearrangement recyclization |
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