Imidazole has two nitrogen atoms.
Imidazole-4,5-dicarboxylic Acid [I45DA] is the scaffold from which the derivatives are synthesized.
However, imidazole doesn’t act like either of them.
A simple highly versatile and efficient synthesis of 2,4,5-trisubstituted imidazoles is achieved by three component cyclocondensation of 1,2-dicarbonyl compounds, aldehydes and ammonium acetate as ammonia source in thermal solvent free condition using Brønsted acidic ionic liquid diethyl ammonium hydrogen phosphate as catalyst. The key advantages of this process are cost effectiveness of catalyst, reusability of catalyst, easy work-up and purification of products by non-chromatographic methods, excellent yields and very short time reactions.
The new results concerning synthesis of some 2,4,5-triaryl-1H-imidazoles in the absence of any additive, as catalyst, is presented. Moreover, we modified the experimental route for the isolation and purification of the un-reacted benzyl, as initial reactant, from products at the end of the reaction.
Imidazole synthesis - Organic chemistry
3. 4-(4,5-Diphenyl-1H-imidazol-2-yl)-phenol (1c): Mp 267–269°C. FTIR (KBr, cm−1): 3590 (OH), 3454 (NH), 3284, 3064, 1701(C=C), 1283; 1HNMR (300 MHz, DMSO-d6): 12.20 (s, 1H, NH), 9.40 (s, 1H, OH), 7.90 (d, J¼8.4 Hz, 2H), 7.52–7.29 (m, 10H, Ar-H), 6.80 (d, J¼8.4 Hz, 2H); 13C NMR (300 MHz, DMSO-d6): 157.6, 146.65, 127.12, 125.7, 124.3, 121.9, 114.75, 112.85, 98.55, 95.46ppm.
4. 2-(4-Methoxyphenyl)-4,5-diphenylimidazole (1d): Mp. 230–232°C. IR (KBr, cm−1): 3400, 3060, 1611, 1490, 1179, 1028, 830, 761; 1HNMR (DMSO-d6, 300MHz): 12.52 (s, 1H, NH), 8.03 (d, J=8.80 Hz, 2.0 Hz, 2H), 7.70-7.10(m, 10H, Ar-H), 7.03 (dt, J=8.8 Hz, 2.0 Hz, 2H), 3.81 (s, 3H, CH3); 13C NMR (300 MHz, DMSO-d6): 158.32, 145.09, 136.01, 134.62, 131.38, 12130, 127.4, 126.01, 123,07, 113.89, 54.62ppm.
Debus-Radziszewski imidazole synthesis - Wikipedia
8. 2-(2-Nitrophenyl)-4,5-diphenyl-1H-imidazole (1h): Mp 230-231°C. FTIR (KBr, cm-1): 3421 (NH), 2928, 1596 (C=N), 1515, 1345, 856. 1H NMR (300 MHz, DMSO-d6): 12.10 (br. S., 1Н, NH), 7.9 - 8.2 (m, 14Н, Ar-H). 13C NMR (300 MHz, DMSO-d6): 147.0, 141.0, 136.1, 130.6, 129.70, 128.4, 127.0, 126.9, 126.1, 125.4, 124.0, 122.0, 118.5ppm.
1. 2,4,5-Triphenyl-1H-imidazole (1a). Mp. 271–272°C. FTIR (KBr, cm−1): 3434 (NH), 2993, 2470, 1638 (C=C), 1510 (C=N); 1H NMR (300 MHz, DMSO-d6): 12.7 (s, 1H, NH), 8.1 (d, J¼7.8 Hz, 2H), 7.1–7.9 (m, 13H, Ar-H); 13C NMR (300 MHz, DMSO-d6): d 146, 136, 135.4, 130.8, 130, 129, 128.75, 128.3, 127.5, 127, 125.6.
Imidazole - definition of imidazole by The Free Dictionary
Imidazole and Benzimidazole Synthesis - 1st Edition
Some imidazole compounds inhibit the biosynthesis of ergosterol, required in cell membrane in fungal.
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Benzimidazole structure is a part of the nucleotide portion of vitamin B
Imidazole | definition of imidazole by Medical dictionary
Some imidazole analogues which contain nitrogen in five-membered ring structure are:
Looking for online definition of imidazole in the Medical Dictionary
Synthesis of 1-substituted 2, 4, 5 triphenyl imidazoles: It was synthesized by refluxing 2,4,5- triphenyl imidazole and acid chloride by using benzene as solvent and pyridine as a catalyst for 4-5 hrs. The product was isolated, dried and recrystallized from ethanol.
Meaning of imidazole medical term
11. 2-(2,6-Dichlorophenyl)-4,5-diphenyl-1H-imidazole (1k): Mp 228-231°C. FTIR (KBr, cm-1): 3390(NH), 3055(C-H), 2962, 2830, 1679 (C=N), 1559, 1194, 1096, 765, 695. 1HNMR (DMSO-d6, 300MHz): 11.82 (br. S., 1Н, NH), 7.79-7.94 (m., 13H); 13C NMR (300 MHz, DMSO-d6): 160.737, 157.104, 151.345, 143.150, 135.289, 134.312, 131.166, 129.592, 129.392, 129.306, 128.224, 128.186, 128.115, 127.234, 127.122, 126.661, 126.453, 126.262, 111.751, 105.380, 98.151ppm.
Imidazole Synthesis | Aldehyde | Pyridine - Scribd
Synthesis of 2, 4, 5- triphenyl imidazole: It was synthesized by refluxing benzil, benzaldehyde with ammonium acetate in acetic acid medium at 100°C for 5-24 hrs.
Synthesis of imidazole-based NHC–Au(I) complexes and …
The same is true for the activation of Fmoc-His(Trt)-OH since racemization catalyzed by the nitrogen of the imidazole ring may occur. For the coupling of especially bulky amino acids such as Aib, Tic, ... or in the case of recognized difficult coupling we recommend the replacement of HOBt by HOAt, or the use of other activating agents.
Imidazole - Synthesis & Reactions - YouTube
We report here a simple, mild and efficient method for the preparation of the 2,4,5-triarylimidazoles using diethyl ammonium hydrogen phosphate as Brønsted acidic ionic liquid catalyst that is considered as efficient and reusable catalyst. The procedure reported herein is not cumbersome; consequently, the methodology represents a good addition to the list of methods available for the synthesis of highly substituted imidazoles.
Imidazole CAS 288-32-4 | 814223
13. 2-(4-Chlorophenyl)-4,5-diphenyl-1H-imidazole (1m): Mp 262-264°C. FTIR (KBr, cm-1): 3148 (NH), 3082(C-H), 2959, 2912, 1601(C=N), 1502, 1128, 1072, 730, 694, 634. 1HNMR (DMSO-d6, 300MHz): 10.544 (br. S., 1Н, NH), 8.11 (d, J¼8.4 Hz, 2H, Ar-H), 7.294-7.562 (m, 12H, Ar-H); 13C NMR (300 MHz, DMSO-d6): 144.428, 137.296, 135.008, 132.748, 130.927, 129.201, 128.772, 128.667, 128.562, 128.429, 128.200, 127.857, 127.075, 126.837, 126.598ppm.
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