A new efficient protocol for diastereoselective three-component one-pot lactam synthesis involving in situ generation of imines via Staudinger/aza-Wittig tandem combined with Wolff-rearrangement and ketene-imine cycloaddition was developed to produce a...
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The last decade has been characterized by the development and approval of pretomanid and delamanid, which are nitroimidazole based drugs for multidrug resistant tuberculosis. This attracted renewed attention to the nitroheterocyclic scaffolds as a source of safe and efficient antimicrobial agents. While the primary focus is still on nitrofurans and nitroimidazoles, well known as bioreducible prodrugs, a number of studies have been published on other 5-membered nitroheteroaromatic compounds. The latter not only show promising antimicrobial activity, but also demonstrate modes of action different from the conventional reductive activation of nitro group. Considering the potential of these efforts to impact in the continuing race against drug-resistant pathogens, herein we review non-furan/imidazole based 5-membered nitroheteroaromatics investigated as antimicrobial agents in 2010-2020.
3-Aryl glutaric acid anhydrides have been explored as substrates for the Castagnoli-Cushman reaction with imines. A series of 3-aryl glutaric acids was synthesized according to literature protocols and introduced into the reaction with imines in the presence of acetic anhydride. The latter acted as a dehydrating agent leading to in situ generation of a cyclic anhydride from the dicarboxylic acid starting material. Reassuringly, the reaction gave the desired δ-lactams with three newly created stereocenters as predominantly one diastereomer whose relative configuration was established by single-crystal X-ray crystallography.Scheme 3. Synthesis of carboxylic esters 12 a-p via the CCR followed by esterification.
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