Iridium-Catalyzed Direct Amidation of Imidazoles at the C-2 Position with Isocyanates in the Presence of Hydrosilanes Leading to Imidazole-2-Carboxamides was written by Fukumoto, Yoshiya;Shiratani, Motohiro;Noguchi, Hikaru;Chatani, Naoto. And the article was included in Synthesis in 2021.Application In Synthesis of 1-Methylbenzimidazole This article mentions the following:
Regioselective synthesis of imidazole-2-carboxamides such as I [R = Me, CH2OMe, Ph, Bn; R1 = n-hexyl, cyclohexyl, Ph, 1-adamantyl, Bn; R2 = 5-tBu, 5-Ph, 5,6-diMe, etc.] via iridium-catalyzed amidation of imidazoles with isocyanates in the presence of a stoichiometric amount of hydrosilanes was reported. Imidazoles bearing an (O-silyl)carboximidate group at the 2-position appear to be initially formed in the reaction, these were then hydrolyzed to the final products in situ. The addition of the hydrosilane was essential for the catalytic reaction to proceed. Substituents on the imidazole ring had no effect on the reaction, except for certain bulky substituents such as tBu and Ph groups at the 4-position. Triazoles such as 4-methyl-4 H-1,2,4-triazole and 1-methyl-1 H-1,2,4-triazole were also applicable to this C-H amidation and the latter reaction proceeded regioselectively at the carbon atom between the sp3and sp2 nitrogen atoms of the ring, and not between the two sp 2nitrogen atoms. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Application In Synthesis of 1-Methylbenzimidazole).
1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Application In Synthesis of 1-Methylbenzimidazole
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem