The 2-position of imidazolium cations is known to be relatively acidic, leading to the useful Arduengo-type carbenes. At the same time, the acidity of this site can lead to undesired side reactions when using imidazolium-based ionic liquids as solvents. In this note, we describe the surprisingly facile deuterium exchange at this position and also the synthesis and exchange under modestly basic conditions (triethylamine) of a series of 2-methyl-substituted compounds.

[reaction: see text] Fructose has been used as the starting material for the preparation of a new class of room-temperature ionic liquids (RTILs). These liquids exhibit tunable solvent properties much like conventional imidazole-based RTILs. They have been applied as recyclable solvents for the Heck reaction of aryl iodides.

[structure: see text] We report a homogeneous supported version of Koser's salt based on a room-temperature ionic liquid (RTIL) support. By altering the nature of the RTIL, a material was developed that was stable, recyclable, and readily separable from the tosyloxylated ketone products just by using variations in solvent polarity. A similar approach should be applicable to a wide range of supported catalysts and reagents.

Worldwide research efforts in drug discovery involving HIV integrase have produced only one compound, raltegravir, that has been approved for clinical use in HIV/AIDS. As resistance, toxicity and drug-drug interactions are recurring issues with all classes of anti-HIV drugs, the discovery of novel integrase inhibitors remains a significant scientific challenge. We have designed a lead HIV-1 strand transfer (ST) inhibitor (IC50 70 nM), strategically assembled on a pyridinone scaffold. A focused structure-activity investigation of this parent compound led to a significantly more potent ST inhibitor, 2 (IC50 6 ± 3 nM). Compound 2 exhibits good stability in pooled human liver microsomes. It also displays a notably favorable profile with respect to key human cytochrome P450 (CYP) isozymes and human UDP glucuronosyl transferases (UGTs). The prodrug of inhibitor 2, i.e., compound 10, was found to possess remarkable anti-HIV-1 activity in cell culture (EC50 9 ± 4 nM, CC50 135 ± 7 μM, therapeutic index = 15,000).

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