New Related Reactions of 2-Phenylimidazole

Substitution reaction on 1-nitrogen atom (N-1) on imidazole ring

The unshared electron pairs contained in N-1 on the imidazole ring can participate in ring conjugation, reducing the electron density of nitrogen atoms. The hydrogen there is easily replaced. Sharghi et al. reported a synthesis method of 1, 2-diphenyl-1H-imidazole, that is, DMSO at 110 °C, As a reaction solvent, the yield of the product was about 70% after the reaction for 36 h. The reaction process is shown in the figure below.

A similar substitution reaction is shown below:

Complexation reaction of the 3-position nitrogen atoms (N-3) on the imidazole ring with the metal

2-phenylimidazole compounds such as aromatic-imidazole, can easily form multi-dentate complexes with metal ions to form functional materials with chemical and physical properties of both imidazole and metal ions, Such as dichlorodiphenyl imidazole cobalt (II); dichlorodiphenyl imidazole Mn (II); dichlorodiphenyl imidazole Ni (II); dichlorodiphenyl imidazole Fe (II). N-3 on the imidazole ring provides electrons in these reactions, as shown in the figure below.

Conformation of the imidazole ring

Protons on the imidazole ring-NH-group can migrate rapidly between N-1 and N-3. This feature allows the occurrence of 4-and 5-substitution imidazole, as shown in the figure below.

Substitution reaction on the benzene ring

2-phenylimidazole contains the benzene ring backbone, enabling it to undergo substitution reactions in the benzene ring. Pascal Eisele, As proposed by et al. A method of selective deuterium generation of multifunctional organic molecules with D2O as the deuterium source, CuI, KOH and zinc powder as additives under the catalysis of [RuCl2 (PPh 3) 3], as shown in the figure below.

Restitution of C-4 or C-5 on the imidazole ring

In general, when C-2 on the imidazole ring, C-4 or C-5 on the imidazole ring reacts. Due to the interaction of the imidazole rings, the results occurring in C-4 or C-5 are the same.2-benzyl imidazole can be stirred with 1-bromo-2,5-pyrrolidine dione in solvent dimethylformamide (DMF) for 12 h at 0 C to obtain 4,5-dibromo-2-benzyl imidazole, as shown in the figure below.

As shown below, 4,5-dibromo-2-phenylimidazole can react with the electrophile at C-4 or C-5. An efficient scheme for an unprotected haloimidazole under palladium-catalyzed Suzuki-Miyaura cross-coupling reaction was reported by Tan et al. The reaction conditions were relatively mild, through which various functional imidazole derivatives could be obtained.


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