Synthesis of new arylidene derivatives of 3-aminorhodanine

(Z)-3-Amino-5-(pyridin-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-4-one

“…Similar results were also reported by Petlichnaya and co-workers [11][12][13][14][15][16]. These authors found that 3-aminorhodanine exists in two tautomeric forms ( Figure 2).…”

“…Therefore, we tried to prepare and characterize the compound within our studies. Its structure ( Figure S1) was corroborated by 1 H-NMR spectrum ( Figure S2), 13 C-NMR spectrum ( Figure S3) and HRMS ( Figure S4), and the purity confirmed by elemental analysis.…”

Synthesis and Anticancer Activity Evaluation of 5-[2-Chloro-3-(4-nitrophenyl)-2-propenylidene]-4-thiazolidinones

“…For compound 2g, these signals were slightly shifted into a strong magnetic field and appeared as two singlets at 6.89 and 7.19 ppm and two doublets at 7.23 and 7.51 ppm. In the 13 C-NMR spectra of rhodanine derivatives signals of C=O and C=S groups of the core heterocycle were characteristic and appeared at 158.7-174.4 and 193.5-199.3 ppm, respectively.…”

“…The starting 2,4-thiazolidinedione 1a and 2-thioxo-4-thiazolidinone (rhodanine) derivatives 1b-l were obtained according to described procedures. We used three synthetic approaches to this end: (1) [2+3]-cyclocondensation of chloroacetic acid with thiourea (1a [11]) or ammonium thiocyanate (1b [12]); (2) dithiocarbamate method of 3-substituted 2-thioxo-4-thiazolidinone (rhodanine) derivatives synthesis (1c [13], 1g-l [14][15][16][17][18][19]); (3) the reaction of trithiocarbonyl diglycolic acid with amino compounds (1d-f [20,21]). Target Ciminalum-thiazolidinone hybrid molecules 2a-l were synthesized via the Knoevenagel condensation of (2Z)-2-chloro-3-(4-nitrophenyl)prop-2-enal and appropriate 4-thiazolidinone in the presence of sodium acetate under reflux in acetic acid (Figure 2).…”

Synthesis and evaluation of new isatin-aminorhodanine hybrids as PIM1 and CLK1 kinase inhibitors

“…Encouraged by the success of the above reaction, we became interested in the mechanism. Several condensation examples of Naminorhodanine with aldehyde or ketone derivatives have been reported in literature [24] Depending on the reaction conditions, Naminorhodanine can react with aldehyde or ketone derivatives either at the C-5 position through a condensation reaction to form the 5-(aryl)alkylidene compound [25,26] or with primary amine group to conduct to the Schiff base derivative. The former reaction, known as Girard's method is usually favored in ammoniacal medium while heating in alcohols or in the presence of acid catalysis as glacial acetic acid or hydrochloric acid gives usually the Schiff base compounds as illustrated in Scheme 4.…”