Synthetic Routes to Selected Heterocycles Containing Antipyrine Moiety

Abstract

This review deals with the synthetic potentiality and utility of antipyrine and its derivatives in the synthesis of 4-substituted antipyrine and other heterocycles containing antipyrine moiety such as thiazole, pyrazolopyridines, pyrazolopyrimidines, and pyrazolotriazines. The reactions that cover the methods of synthesizing the aforementioned heterocycles such as addition, condensation, and cyclization were also reviewed.

Derivational, Structural, and Biological Studies of Some New Pyrazolyl, Isoxazolyl, Pyrimidinyl, Pyridazinyl, and Pyridopyridazinyl from 4‐Substituted Antipyrine

“…The solid products formed were collected by filtration, dried, and recrystallized from ethanol. Synthesis of (E)-3-(3,5-diamino-4-((1,5-dimethyl-3-oxo-2phenyl-2,3-dihydro-1H-pyrazol-4-yl)diazenyl)-1H-pyrazol-1yl)propanenitrile (8). A solution of compound 3 (3.12 g, 0.01 mol) in pyridine (20 mL) and water (5 mL) was treated with acrylonitrile (0.38 mL, 0.01 mol).…”

“…Design and synthesis of heterocyclic compounds that exhibited potential effects against pathogenic bacteria and fungi are the main target of many medicinal chemists [1][2][3][4], because of the increasing microbial resistance to antibiotics. Heterocyclic compounds that exhibited a wide range of biological applications are exemplified in the literature, that is, nitrosoantipyrine, 4-aminoantipyrine, aminopyrine, and dipyrone (Novalgin) [5][6][7][8][9]. Compounds containing antipyrine moiety were applied in the fields of medicinal [10][11][12][13][14][15][16] and pharmacological properties [17].…”

“…4‐Aminoantipyrine can be used as potent analgesic drug to inhibit cyclooxygenase and as a reagent for biochemical reactions producing peroxides or phenols . Recently, El‐Taweel and Abou Elmaaty have reported a review on the synthetic routes to heterocycles containing antipyrine moiety based on some reactions of 4‐aminoantipyrine and related compounds. In view of the previously mentioned facts and in connection with our ongoing studies of new heterocyclic compounds that may have less toxic properties and great antimicrobial effect , our aim in this work is to report that the synthesis of novel isoxazole, diaminopyrimidine, pyridazine, and pyrido[3,2‐ c ]pyradizine compounds incorporated antipyrine moiety and evaluate the biological activity of these compounds as antimicrobial and antifungal activities.…”