SYNTHESIS, CONFORMATIONAL ANALYSIS AND ANTITUMOR TESTING OF 5-(Z)-ARYLIDENE-4-IMIDAZOLIDINONE DERIVATIVES

Mechanism of the recyclization of 2-amino-5-benzylidene-1,3-thiazol-4(5H)-one into derivatives of 2-amino-5-benzylidene-1,5-dihydro-4H-imidazol-4-one

“…The reaction mixture was left at about 20°C for 12 h. The precipitate formed was filtered off, washed with 1:1 petroleum ether-ethanol, and treated consecutively with boiling acetone and 2-propanol. The precipitate, which formed from the 2-propanol solution after 48 h, was recrystallized from 2-propanol to give 0.24 g (9%) 3a, mp 220-221°C (mp 232°C for the Z-isomer [6]). …”

“…IR spectrum (neat), ν, cm -1 : 3437, 3113 (N-H), 1706 (C=O), 1643 (C=N). 1 H NMR spectrum, δ, ppm (J, Hz): 11.24 (1H, s, NH); 7.96 (2H, d, J = 6.8, arom); 7.30 (2H, t, J = 7.3, arom); 7.18 (1H, t, J = 7.9, arom); 6.30 (1H, s, =CH 6 Compound 4a (1.18 g, 3.43 mmol) in 2-propanol was heated at reflux until completed dissolved and then heated at reflux for an additional 10-15 min. The precipitate formed upon cooling was recrystallized from toluene to give compound 4a (0.449 g, 51.3%); mp 200°C (for the Z-isomer, mp 232°C [6]).…”

“…Compound 1 (1.00 g, 4.90 mmol) in morpholine (4.60 g, 4.60 ml, 52.8 mmol) was heated for ~10 min until the starting reagent dissolved completely. After 48 h, the precipitate formed was filtered off, washed with acetone, and recrystallized from 2-propanol to give compound 3a (0.132 g, 10.5%); mp 210°C (for the Z-isomer, mp 232°C [6]). IR spectrum (neat), ν, cm -1 : 3437, 3113 (N-H), 1706 (C=O), 1643 (C=N).…”

Design, synthesis, molecular docking and cytotoxicity evaluation of some novel 5-arylidene-3-(substituted phenyl)-2-(p-tolylamino)-4-imidazolones

“…Furthermore, 5-arylidene-2-methylthio-3-(substituted phenyl)-3,5-dihydro-4H-imidazol-4-ones 7a-f were synthesized in excellent yields via the reaction of 5a-f in aqueous KOH and methanol with methyl iodide (6) at room temperature (Khodair et al, 1998). 1 H-NMR spectra confirmed the structures of 7a-f, the dissapearence of the singlet signal of NH revealed the Smethylation, also the presence of a singlet signal at 2.63-2.74 ppm that assigned for S-CH 3 confirmed the same result.…”

Facile synthesis of 2‐alkylthio‐3‐amino‐4 H‐imidazol‐4‐ones and 2H‐imidazo[2,1‐b]‐1,3,4‐thiadiazin‐6(7H)‐ones via N‐vinylic iminophosphorane

“…Efforts to discover new biologically active derivatives are reflected by the still important number of publications and patents devoted to the subject [4][5][6][7][8]. For example, some 2-alkylthio substituted 4H-imidazol-4-ones show significant antifungal and antibacterial activities [5,6], whereas others exhibited good antitumor and antiviral activities [7,8]. However, most of the 2-alkylthio-3-aminoimidazolones reported are of the 5,5-disubstituted type and were generally synthesized from corresponding ␣-amino acetic acid [1,2] (Eq.…”