Thei ntramolecular cyclization of allylamines and ketones was achieved in the presence of potassium tert-butoxide and N,N-dimethylformamide.As eries of 4-arylquinolines was prepared in good yields.T he reactionc ould be accomplisheda t room temperature using only as ubstoichiometric amount of potassium tert-butoxide.O nt he other hand, the reactiono ft he structurallya nalogous allyl ethers affordedd iverse products.T he reaction may proceed via the rearrangement of a-aminoallyl radicals and the generation of nucleophilic enamine intermediates.T his findingr epresents an ew strategy for the synthesis of quinoline derivatives from readily available 2-(allylamino)phenyl ketones.Scheme 1. Reactions of substrates 1s-1v.Scheme2.Te ntative reaction mechanism. 3476 asc.wiley-vch.de
A series of 3-amino-5-benzylphenol derivatives were designed and synthesized. Among them, (3-benzyl-5-hydroxyphenyl)carbamates were found to exert good inhibitory activity against M. tuberculosis H37Ra, H37Rv and clinically isolated multidrug-resistant M. tuberculosis strains (MIC = 0.625–6.25 μg/mL). The privileged compounds 3i and 3l showed moderate cytotoxicity against cell line A549. Compound 3l also exhibited potent in vivo inhibitory activity on a mouse infection model via the oral administration. The results demonstrated 3-hydroxyphenylcarbamates as a class of new antitubercular agents with good potential.
A series of (3‐benzyl‐5‐hydroxyphenyl)carbamates were evaluated as new antibacterial agents. Several compounds showed potent inhibitory activity against sensitive and drug‐resistant Gram‐positive bacteria. The compounds are ineffective against all tested Gram‐negative bacteria. The structure of the ester group exerted a profound effect on antibacterial activity. 4,4‐Dimethylcyclohexanyl carbamate 6h exhibited the most potent inhibitory activity against the standard and clinically isolated Staphylococcus aureus, Staphylococcus epidermidis, and Enterococcus faecalis (minimum inhibitory concentration = 4–8 µg/ml) strains. The preliminary experimental evidence indicated that these carbamates target the bacterial cell wall and share a similar mechanism of action with vancomycin.
Concise Synthesis of 4-Arylquinolines via Intramolecular Cyclization of Allylamines and Ketones. -In most cases, the title reaction yields the expected products under the mild conditions A). Only the substrate (VII) produces an indole instead of the required quinoline. Extension to oxygen-containing educts is also investigated where different types of products are formed. -(WEI, W.-T.; CHENG, Y.-J.; HU, Y.; CHEN, Y.-Y.; ZHANG, X.-J.; ZOU, Y.; YAN*, M.; Adv. Synth. Catal. 357 (2015) 16-17, 3474-3478, http://dx.
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