Synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles in water using p-dodecylbenzenesulfonic acid as catalyst
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Benzil
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
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Abstract A series of 2‐aryl‐4,5‐diphenylimidazoles were synthesized by a one‐step condensation reaction of benzil, aromatic aldehyde, and ammonium acetate in acetic acid under microwave irradiation. The reactions were completed in 4–11 min with good yields and easy workup.
Benzil
Condensation reaction
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An efficient and a quick microwave-assisted synthesis of benzimidazoles and trisubstituted imidazoles was developed. Three benzimidazoles were obtained as a result of the condensation of 1,2-phenylenediamine with carboxylic acids and acetoacetic ester without catalyst. A series of trisubstituted imidazoles were synthesized by condensation of benzil, aromatic aldehyde and ammonium acetate in the presence of glacial acetic acid.
Benzil
Condensation reaction
Benzimidazole
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Nano TiO2 supported on SiO2 (Nano TiO2@SiO2) as a solid Lewis acid, was described to be an effective and reusable catalyst for one-pot three-component reaction of benzil, aryl aldehydes and ammonium acetate for the synthesis 2-aryl-4,5-diphenyl1H-imdazoles synthesis. To explore the high efficacy of the catalytic system the four -component cyclization of benzil, aryl aldehydes, ammonium acetate and anilines has also been accomplished successfully to obtain their 1,2 -diaryl-4,5-diphenyl-1Himidazole adducts. A plausible mechanism has also been expressed. The catalyst has been recovered and its reusability confirmed in 4 runs. High yields, simple operation, easy -work procedure, mild reaction conditions in addition with the reusability are some advantages of this protocol.
Benzil
Reusability
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Abstract Phosphorus pentoxide supported on silica gel (P 2 O 5 /SiO 2 ) has been used as an efficient and reusable catalyst for the one‐pot pseudo four‐component synthesis of 2,4,5‐trisubstituted imidazoles from benzil or benzoin, aldehydes, and ammonium acetate. It was also used for four‐component preparation of 1,2,4,5‐tetrasubstituted imidazoles from benzil or benzoin, aldehydes, primary amine, and ammonium acetate under thermal solvent‐free conditions. The remarkable features of this new procedure are high conversions, cleaner reaction, simple experimental and work‐up procedures and also the catalyst can be easily separated from the reaction mixture and reused several times without any loss of its activity.
Benzil
Benzoin
Phosphorus pentoxide
Component (thermodynamics)
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Abstract Natural scolecite has been found as an effective catalyst for the one-pot synthesis of 2,4,5-triarylimidazole derivatives via a three component reaction using benzil or benzoin, aldehydes and ammonium acetate. This method provides several advantages such as being environmentally benign, reusable, possessing high yields with increased variations of the substituents in the product and preparative simplicity.
Benzil
Benzoin
Simplicity
Component (thermodynamics)
Natural product
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Bis(p-methoxyphenyl)-4,4′-5,5′-tetraphenyl-1,2′-biimidazole (2) was prepared from benzil, p-methoxybenzaldehyde and ammonium acetate. Experiments were done under different reaction conditions, and the optimal conditions were determined. In acetic acid, as mole ratio of benzil, p-methoxybenzaldehyde and ammonium acetate was 1∶1∶8, 93.6% of 2-(p-methoxyphenyl)-4,5-diphenylimidazole (1) was obtained after refluxing for 3 h. When reaction temperature was 0～15 °C, 1 was dissolved in HOCH_2CH_2OCH_2CH_3 and mole ratio of 1 to K_3[Fe(CN)_6] was 1∶2, the yield of 2 was 87.5% after reacting for 5 h.
Benzil
Mole
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Abstract The multicomponent cyclocondensation of benzil with aromatic aldehydes, an amine and ammonium acetate (or ammonium acetate alone) is efficiently catalyzed by SiO 2 ‐supported Wells—Dawson heteropolyacid to give the polysubstituted imidazole derivatives (IV) and (VI) in high yields.
Benzil
Imidazole
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Fifteen substituted 2,4,5-triaryl-1H-imidazoles are synthesized by three-component and one-pot reaction of aromatic aldehydes,benzil and ammonium acetate under microwave irradiation,solvent and catalyst-free conditions.The products are identified by IR,1HNMR,13CNMR and MS.The method is in accordance with the requirement of green chemistry.
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
Benzil
Trifluoromethanesulfonate
Ytterbium
Component (thermodynamics)
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