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Synthesis 1994; 1994(12): 1437-1440
DOI: 10.1055/s-1994-25709
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Synthesis of 3-Substituted-7-alkoxy-5H-pyrazolo[4,3-d]-1,2,3- triazin-4-(3H)-ones

Pier Giovanni Baraldi* , Laura Garuti, Marinella Roberti
  • *Dipartimento di Scienze Farmaceutiche, Università di Ferrara, I-44100 Ferrara, Italy
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Publication Date:
25 April 2002 (online)

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An efficient method for the preparation of 3-substituted-7-alkoxy-5H- pyrazolo[4,3-d]-1,2,3-triazin-4(3H)-ones 7a-n is described. Isopropyl 1,4-dinitropyrazole-5-carboxylate (2) underwent aromatic nucleophilic "cine" substitution with concomitant ester hydrolysis to give 3(5)-alkoxy-4-nitropyrazole-5(3)-carboxylic acids 3a-c, when it was reacted with an alcoholic solution of potassium hydroxide at room temperature. The latter were converted into the final compounds 7a-n through a four step sequence, involving: i) carboxylic acid activation, ii) carboxamide formation, iii) nitro group reduction, and iv) intramolecular diazotization.