An Efficient and Convenient Synthesis of Certain 2-Thioxothiazole,2-oxo-1,2-dihydropridine, 2-Oxo-2<i>H</i>-pyran,2,4-diaminothiophene and Pyrazolo[5,1-c][1,2,4]triazine Derivatives Containing Antipyrine Moiety

Abstract

ABSTRACT2-Thioxothiazole derivatives 5a-c were prepared by reacting a mixture of 1a-c, CS 2 /KOH and 4-(2-chloroacetyl)-1,

Synthetic Routes to Selected Heterocycles Containing Antipyrine Moiety

“…On the other hand, compound 76 reacted with mercaptoacetic acid in dry pyridine to give N ‐[4‐(4‐antipyrinyl)‐2‐thioxothiazol‐3(2 H )‐yl]‐2‐(4‐oxo‐4,5‐dihydrothiazol‐2‐yl)acetamide 77 . Coupling of 76 with aryl diazonium salts yields 2‐arylhydrazone derivatives 78 (Scheme ).…”

“…Also, reaction of 4‐chloroacetylantipyrine 17 with benzoylacetonitrile and phenyl isothiocyanate in dimethylformamide containing potassium hydroxide afforded 2‐benzoyl‐3‐anilino‐3‐(antipyrinoylmethylthio)acrylonitrile 79 . Cyclization of 79 by refluxing in ethanol/triethylamine afforded 4‐(2‐antipyrinoyl‐5‐anilino‐3‐phenylthiophene)cabonitrile 80 (Scheme ).…”

“…Antipyrine (1‐phenyl‐2,3‐dimethylpyrazol‐5‐one) 1 and its derivatives play an important role in heterocyclic synthesis as they are of great biological and medicinal value . They are important pyrazolone derivatives and have been widely used for a long time in medicine as antipyretic , analgesic , sedative , antimicrobial , antiviral , antioxidant , anticancer , and anti‐inflammatory drugs .…”

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

“…Design and synthesis of heterocyclic compounds that exhibited potential effects against pathogenic bacteria and fungi are the main target of many medicinal chemists , 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) . Compounds containing antipyrine moiety were applied in the fields of medicinal and pharmacological properties .…”

Mercaptoacetic Acid

“…1 It is widely described in the literature, especially as a substrate for the synthesis of pharmacologically active heterocycles 2 including 1,3-thiazolidin-4-ones, 3 1,4-thiazepines 4 and thiazoles. 5 It is also used for the formation of spiro derivatives, 6 in multicomponent reactions, and in removing the nosyl protecting group from amine functions of α-amino acids. …”