A One-Pot, Four-Component Synthesis of N-Substituted 2,4-Diarylimidazoles

Abstract

A one-pot, four-component synthesis of 1,2,4-trisubstituted 1H-imidazoles is described. Heating a mixture of a 2-bromoacetophenone, an aldehyde, a primary amine, and ammonium acetate under solvent-free conditions affords functionalized imidazoles in good to excellent yields.

Multicomponent Synthesis of 2-[Aryl(arylamino)methyl]furo[3,2-c]pyran-3,4-diones and Diastereoselective Furan Ring Opening to (Z)-3-[3-Aryl-3-(arylamino)acryloyl]-4-hydroxypyran-2-ones

“…11,12 It was also possible to convert the synthesized furo[3,2-c]pyran-3,4-diones 4a-h totally into their furan ring-opened tautomers 5a-h with similar yields by using ammonium acetate as base in refluxing ethanol for 30 minutes (Scheme 1). The formation of the expected imidazole ring does not occur following the previously reported four-component reaction, 8 where ammonium acetate offers a second nitrogen to the final imidazole-lactone dyad (Scheme 1). All in all, we have discovered a new three-component preparation of aniline-functionalized furo[3,2-c]pyran-3,4-diones 4a-h and their possible base-catalysed tautomerism into 3-enaminone-pyran-2-ones 5a-h using ammonium acetate.…”

Practical Synthesis of Polysubstituted Imidazoles via Iodine‐ Catalyzed Aerobic Oxidative Cyclization of Aryl Ketones and Benzylamines

“…1‐Benzyl‐4‐(4‐bromophenyl)‐2‐phenyl‐1 H ‐imidazole 26 (4ja): White solid, mp 152–154 °C. 1 H NMR (400 MHz, CDCl 3 ): δ =7.66 (d, J =8.5 Hz, 2 H), 7.58–7.55 (m, 2 H), 7.42 (d, J =8.5 Hz, 2 H), 7.38–7.25 (m, 6 H), 7.15 (s, 1 H), 7.06 (d, J =8.0 Hz, 2 H), 5.11 (s, 2 H); 13 C NMR (100 MHz, CDCl 3 ): δ =148.6, 140.2, 136.5, 132.9, 131.4, 130.1, 128.9, 128.8, 128.7, 128.5, 127.9, 126.5, 126.3, 120.2, 116.9, 50.3; HR‐MS (ESI): m/z =389.0637, calcd.…”

“…2,4‐Diphenyl‐1‐propyl‐1 H ‐imidazole 26 (4aab): White solid, mp 87–89 °C. 1 H NMR (400 MHz, CDCl 3 ): δ =7.85 (d, J =7.2 Hz, 2 H), 7.63 (d, J =7.7 Hz, 2 H), 7.49–7.36 (m, 5 H), 7.31 (s, 1 H), 7.24 (t, J =7.4 Hz, 1 H), 3.97 (t, J =7.6 Hz, 2 H), 1.86–1.76 (m, 2 H), 0.91 (t, J =7.4 Hz, 3 H); 13 C NMR (100 MHz, CDCl 3 ): δ =148.1, 141.1, 134.2, 131.0, 129.1, 128.8, 128.6, 128.5, 126.6, 124.9, 116.0, 48.5, 24.4, 11.1; HR‐MS (ESI): m/z =263.1542, calcd.…”

Identification of novel antifungal agents: antimicrobial evaluation, SAR, ADME–Tox and molecular docking studies of a series of imidazole derivatives

“…Members of this family of compounds have diverse biological, pharmacological, environmental and industrial applications [14]. Indeed, this type of compounds act as inhibitors of p38 MAP kinase and B-Raf [15], and showed anti-inflammatory, anti-cancer, antifungal, anti-tuberculosis, and anti-diabetic activities [16–18]. Accordingly, several imidazole-based heterocyclic compounds have been clinically used to treat many diseases such as Bifonazole which is a clinically used antifungal agent with a broad spectrum of activity [19, 20], Metronidazole used to treat a wide variety of bacterial and parasitic infections [21], Cimetidine used in the treatment of duodenal and gastric ulcers [22], and Eprosartan used as angiotensin II inhibitor and antihypertensive agent [23].…”