Urea–Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel

Abstract

The low-melting mixture urea–ZnCl2 was evaluated as a novel reaction medium for the synthesis of imidazoles. The reaction between a dicarbonyl compound, ammonium acetate, and an aromatic aldehyde is efficiently catalyzed by the eutectic solvent, yielding a wide variety of triaryl-1H-imidazoles or 2-aryl-1H-phenanthro[9,10-d]imidazoles in good to excellent yields. In addition, the eutectic solvent was reused in five cycles without loss of its catalytic activity. This protocol was further explored for the synthesis of the drug trifenagrel, giving an excellent yield.

One-pot, three-component, iron-catalyzed synthesis of benzimidazolesviadomino C–N bond formation

“…Finally, the desired benzimidazole is generated by [1,5]-H shi (VI) and the Fe(III) porphyrin catalyst is regenerated to start the next cycle. 2,49…”

Dopant-free small-molecule hole-transport material for low-cost and stable perovskite solar cells

“…Preparation of phenanthroimidazole derivatives was accomplished using a one-pot cyclizing reaction via a very simple route without the use of a catalyst or column chromatography purification. [73][74][75][76][77] The experimental details, including the methods and synthesis procedure for the HTMs, are presented in ESI, † S1 and S2. The molecular structures of the perovskite/ HTMs are shown in Scheme 1.…”

Synthesis, Characterization, Molecular Docking, and Investigation of Antibacterial Properties of New Derivatives of 1‐H‐Phenanthro [9,10‐d] Imidazole

“…The FT-IR spectrum (v, cm À 1 ) of compound 4 a was recorded as a KBr tablet, which contains the desired stretching and bending vibrations. In the FT-IR spectrum of this compound NÀ H stretching vibrations were observed at 3427, CÀ O stretching vibrations at 1272-1497, CÀ H stretching vibrations of the aromatic ring at 3070, C=C stretching vibrations of the aromatic ring at 1461-1651, aliphatic CÀ H stretching vibrations at 2930 [47] 4 b 90 298-301 347-349 [47] 4 c 85 248-250 -4 d 88 150-152 295-298 [48] 4 e 92 244-247 264-265 [49] 4 f 88 190-193 335-337 [47] [50] 4 h 80 160-163 176-179 [51] 4 i 80 181-183 -4 j 83 240-242 245-247 [50] 4k 86 198-200 - [52] 4 m 92 190-192 263-265 [50] 4 n 87 207-209 232-234 [53] 4 o 88 193-195 258-261 [54] 4 p 84 270-272 - [55] 4 s 90 225-228 233-235 [56] 4 t 87 216-218 232-233 [57] 4 u 86 280-282 270-272 [58] Messages related to 8 types of hydrogen were observed. NH amino protons appeared in the low field at 13.33 ppm as a small peak with the area under the peak equal to 1 hydrogen.…”