Transition-Metal-Free Three-Component Reaction: Additive Controlled Synthesis of Sulfonylated Imidazoles

Abstract

Two efficient transition-metal-free highly regioselective pathways for constructing sulfonylated imidazoles via three-component reactions of amidines, ynals, and sodium sulfonates have been developed. The generations of different sulfonylated imidazoles were simply controlled by additives. In addition, this method features environmental friendliness, good functional group tolerance, and high atom economy, which makes it practical.

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

“…Cao and co-workers 351 developed a reagent-controlled efficient transition-metal-free highly regioselective strategy for the synthesis of two different sulfonylated imidazoles via a three-component reaction of amidines, ynals, and sodium sulfinates as presented in Scheme 242 . AcOH mediated various electron-rich and electron-poor N -substituted benzimidamides and formed the corresponding imidazoles in 56–83% yields.…”

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

“…Performance of the reaction in EtOH in the presence of AcOH delivered 4‐sulfonyl derivatives, while conducting the process in MeCN and addition of TBHP as the oxidant resulted in 5‐sulfonyl derivatives (Scheme 193). [241] Apparently, imidazoles 439 are formed through ionic pathway (Scheme 194a). Protonation of the starting ynal 437 and nucleophilic attack of sulfinate 438 leads to intermediate A .…”

Pyromellitic diamide–diacid bridged mesoporous organosilica nanospheres with controllable morphologies: a novel PMO for the facile and expeditious synthesis of imidazole derivatives

“…32,67,68,[72][73][74][75][76][77][78][79][80][81][82][83][84] This bunch of 1,3-diazoles exhibits therapeutic behaviors such as antibiotics, 85,86 antifungals, 87,88 and antagonistic activity. 89 Imidazole compounds are used in some medicines, such as the new Alpidem, [90][91][92] Cimetidine, Etomidate, Ketoconazole, 93,94 antiviral Daclatasvir 95,96 and Nitroimidazole (Fig. 1).…”