55041-14-0

Upstream product

• 24722-30-3 cyclohexanecarboximidamide 
• 447-31-4 Desyl chloride 
• 2227-79-4 benzenecarbothioamide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 134-81-6 benzil 
• 501-65-5 diphenyl acetylene 
• 24242-77-1 α-iodo-α-phenylacetophenone 
• 451-40-1 phenyl benzyl ketone 
• 766-05-2 cyclohexane carbonitrile 
• 484-47-9 lophine 

Relevant academic research and scientific papers

TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions

In the process of drug discovery and development, an efficient and expedient synthetic method for imidazole-based small molecules from commercially available and cheap starting materials has great significance. Herein, we developed a TMSOTf-catalyzed synthesis of trisubstituted imidazoles through the reaction of 1,2-diketones and aldehydes using hexamethyldisilazane as a nitrogen source under microwave heating and solvent-free conditions. The chemical structures of representative trisubstituted imidazoles were confirmed using X-ray single-crystal diffraction analysis. This synthetic method has several advantages including the involvement of mild Lewis acid, being metal- and additive-free, wide substrate scope with good to excellent yields and short reaction time. Furthermore, we demonstrate the application of the methodology in the synthesis of biologically active imidazole-based drugs.

One-Pot, Two-Step Metal and Acid-Free Synthesis of Trisubstituted Imidazole Derivatives via Oxidation of Internal Alkynes Using an Iodine/DMSO System

A one-pot, two-step, simple, efficient and eco-friendly oxidation of internal alkynes as a key step towards the synthesis of 2,4,5-trisubstituted imidazoles, using an inexpensive I2/DMSO system, has been reported. This metal and acid-free synthesis proceeded smoothly to furnish a variety of synthetically useful trisubstituted imidazoles in moderate to excellent yields. In an effort to demonstrate the potential future applications of this system, a double oxidation study was undertaken and the desired trisubstituted imidazoles obtained in good to moderate yields.

An iodine/DMSO-catalyzed sequential one-pot approach to 2,4,5-trisubstituted-1H-imidazoles from α-methylene ketones

A sequential one-pot approach to 2,4,5-trisubstituted imidazoles has been developed from α-methylene ketones and aldehydes. This methodology employs air-moisture stable reaction conditions and an inexpensive iodine/DMSO system affording a diverse range of known and novel (substrate scope) 2,4,5-trisubstituted imidazoles in moderate to excellent yields. The iodine/DMSO system was extended to the domino convergent synthesis of two functionalized intermediates, benzil and benzaldehyde, to produce the final product.

Selenium dioxide mediated benzylic sp3 C-H oxidation in acetic acid: Synthesis of lophine derivatives from α-methylene ketones via a domino multicomponent reaction

We report a selenium dioxide/acetic acid catalysed one-pot conversion of a-methylene ketones to 1,2-diaryldiketones as a key step to successfully access lophine derivatives in a domino multicomponent reaction.

Copper-catalyzed aerobic benzylic sp3 C-H oxidation mediated synthesis of 2,4,5-trisubstituted imidazoles via a domino multi-component reaction

An efficient and practical aerobic benzylic sp3 C-H oxidation as a key step towards the domino multi-component synthesis of 2,4,5-trisubstituted imidazoles has been reported. This green methodology employs an inexpensive catalytic copper/oxygen system and proceeds under mild reaction conditions. A variety of substituted imidazoles are prepared in moderate to excellent yields from α-methylene ketones using this innovative methodology.

Copper-mediated C(sp3)-H azidation with Me3SiN3: Synthesis of imidazoles from ketones and aldehydes

The efficient construction of 2,4,5-trisubstituted imidazoles, through a copper-mediated three-component reaction involving ketones, aldehydes, and Me3SiN3, has been developed. During the process, 4 C-N bonds were formed sequentially. Experimental results and DFT calculations suggested that azidation of the alpha methylene group of the ketone was the key C-N bond-forming step.

A facile strategy for the synthesis of highly substituted imidazole using tetrabutyl ammoniumbromide as catalyst

A simple and facile strategy for the synthesis of highly substituted imidazoles has been developed by multi-component condensation of 1,2-diketone, aldehyde, amine, and ammonium acetate in presence of tetrabutyl ammonium bromide as catalyst. Springer Science+Business Media B.V. 2011.

Catalytic procedures for multicomponent synthesis of imidazoles: Selectivity control during the competitive formation of tri- and tetrasubstituted imidazoles

The catalytic potential of different fluoroboric acid-derived catalyst systems viz. aq HBF4, solid supported HBF4, metal tetrafluoroborates (inorganic salts), solid supported metal tetrafluoroborates, and tetrafluoroborate based ionic liquids (organic salts) were investigated for the three component reaction (3-MCR) of 1,2-diketone, aldehyde, and ammonium salts to form 2,4,5-trisubstituted imidazoles and the four component reaction (4-MCR) involving 1,2-diketone, aldehyde, amine and ammonium acetate to form 1,2,4,5-tetrasubstituted imidazoles. The HBF4-SiO2 was found to be the stand out catalyst for both the 3-MCR and 4-MCR processes. The next most effective catalysts are LiBF4 and Zn(BF4) 2 to form 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles via the 3-MCR and 4-MCR, respectively. This is the first report on the unaddressed issue of competitive formation of 2,4,5-trisubstituted imidazole during the 4-MCR involving 1,2-diketone, aldehyde, amine and ammonium acetate and highlights the influence of the catalyst systems in controlling the selective formation of tetra substituted imidazole. The metal salt of weak protic acids drive selectivity towards tetra substituted imidazole in the order tetrafluoroborates > perchlorates > triflates. The catalytic potency of tetrafluoroborates was in the order Zn(BF4)2 > Co(BF4)2 > AgBF4 ≈ Fe(BF 4)2 > NaBF4 ≈ LiBF4 ≈ Cu(BF4)2. The developed protocols worked well for different diketones, various aryl, heteroaryl, and alkyl aldehydes and in the case of the preparation of 1,2,4,5-tetrasubstituted imidazoles different amines can be used. The effectiveness of different ammonium salts as nitrogen source has been investigated and ammonium acetate is proved to be the best. The HBF4-SiO2 is recyclable for five consecutive uses without significant loss of catalytic activity. The Royal Society of Chemistry 2012.

A convenient method for the preparation of 2,4,5-triaryl imidazoles using barium chloride dispersed on silica gel nanoparticles (BaCl2-nano SiO2) as heterogeneous reusable catalyst

A simple and eco-friendly procedure for the synthesis of 2,4,5-triaryl imidazoles by using Barium chloride dispersed on silica gel nanoparticles (BaCl2-nano SiO2) as heterogeneous reusable catalyst in high yield under thermal conditions has been described.