In this study, we investigated a series of triarylimidazoles, in an effort to elucidate critical SAR information pertaining to their anti-plasmodial and β-hematin inhibitory activity. Our results showed that in addition to the positional effects of ring substitution, subtle changes to lipophilicity and imidazole ionisability were important factors in SAR interpretation. Finally, in silico adsorption analysis indicated that these compounds exert their effect by inhibiting β-hematin crystal growth at the fast growing 001 face.

This article describes a mechanistic investigation into the I-2/DMSO mediated benzylic C-sp(3)-H oxidation of an alpha-methylene ketone. The electron paramagnetic resonance (EPR) spectrum centred at g = 2.0011 supports the involvement of iodine and benzylic radicals, as the alpha-iodinated compound 2-iodo-1,2-diphenylethanone was isolated as a key reactive intermediate. The oxidation reaction relies, primarily, on DMSO as a source of oxygen in benzil, proven by the reaction of benzyl phenyl ketone with diphenyl sulfoxide (DPSO). (C) 2019 Elsevier Ltd. All rights reserved.

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.

An efficient and practical aerobic benzylic sp3C–H oxidation as a key step towards the domino multi-component synthesis of 2,4,5-trisubstituted imidazoles has been reported.

The Doebner-von Miller synthesis of quinolines under solvent-free conditions is described, catalyzed by recyclable Ag(I)-exchanged Montmorillonite K10. The desired products are obtained in good to excellent yields and the reaction accommodates both aromatic and aliphatic alpha,beta-unsaturated aldehydes making this process an attractive method for the synthesis of substituted quinolines. In addition, the Ag(I)-exchanged Montmorillonite K10 catalyst can be recovered and reused up to 5 times with excellent activity.