Reaction of monocyclic ferrocenyl-4,5-dihydropyrazoles with β-dicarbonyl compounds

Abstract

Monocyclic 3-and 5-ferrocenyl-4,5-dihydropyrazoles with a free NH group in the molecule react with acetylacetone to form the corresponding enaminocarbonyl compounds. The latter were isolated as a single isomer, presumably E. 3-Ferrocenyldihydropyrazoles and 5-ferrocenyl-3-(p-methoxyphenyl)-4,5-dihydropyrazole analogously react with acetoacetic ester. 5-Ferrocenyl-3-phenyl-, 3-(p-bromophenyl)-5-ferrocenyl, and 3,5-diferrocenyl-4,5-dihydropyrazoles react with acetoacetic ester to form acetoacetylpyrazolides.

Synthesis, Crystal Structure and Thermal Properties of N-Acetyl-3-(2-furyl)-5-ferrocenyl-2-pyrazoline and N-Acetyl-3-(2-thienyl)-5-ferrocenyl-2-pyrazoline

“…Among the various pyrazoline isomers, 2-pyrazolines are the most frequently investigated compounds due to their important pharmacological properties, mainly as anti-inflammatory, antidepressant, antipyretic, antioxidant, antimicrobial, antifungal, and antitumor agents [4][5][6][7][8][9]. Therefore they are useful materials in drug research.…”

“…Therefore they are useful materials in drug research. Formation of the N-acetyl derivatives of 2-pyrazolines is beneficial since the N-substituted 2-pyrazolines are stable compounds and can be used for biological and pharmaceutical trials without the risk of undesirable decomposition [4][5][6][7][8][9][10]. In addition, N-acetylated-2-pyrazolines found to be useful for the treatment of cancer are inhibitors of kinesin spindle protein (KSP) potentially [11].…”

Synthesis of dihydropyrazole‐bridged dinuclear ferrocenyl derivatives and their catalytic effect on thermal decomposition of ammonium perchlorate

“…The bulky substituent is anticipated to hinder the migration in composite propellants. [10,13,14] Introduction in dihydropyrazole of additional various acyl substituents on the N atom makes the compounds more stable, [15,16] which is a vital property of a burning rate catalyst.…”