| Autor: |
Narula, Dipika, Bari, Shamsher S., Singh, Gulab, Sharma, Rajni, Garg, Ankita, Bhalla, Aman |
| Předmět: |
|
| Zdroj: |
Journal of Sulfur Chemistry; Dec2023, Vol. 44 Issue 6, p712-732, 21p |
| Abstrakt: |
The regioselective benzoyloxylation process involves stirring a mixture of phenyl/benzyl-sulfanyl/selenylethanoate 1a-c with appropriate oxidant [benzoyl peroxide (BPO) 2a/ m-chloroperbenzoic acid (m-CPBA) 2b /bis(p-methoxybenzoyl peroxide) (BPM-BPO) 2c] under catalysis of hydrated copper acetate in toluene at 60 °C/RT. Regioselective C–H functionalization of esters 1a-c leads to benzoyloxy substituted phenyl/benzyl-sulfanyl/selenylbisesters 3a-g in good to excellent yields (80–95%). Variably substituted trans-3-phenylsulfanyl-β-lactams 4 employed for C3-H functionalization with BPO 2a generates diastereoisomeric mixture of trans- and cis-3-benzoyloxy-3-(phenylsulfanyl)-β-lactams 5 and 6 as major and minor isomers after efficient column chromatographic purification. The structural confirmation was done using IR, 1H NMR, 13C NMR, DEPT-90 NMR spectroscopic analysis and CHNS elemental analysis. In vitro antibacterial and antifungal evaluations on bisesters suggest benzylselenyl-bisester 3c as potent antimicrobial agent. Out of trans- and cis-3-benzoyloxy-β-lactams 5a and 6a, the trans isomer 5a was active against all microbial strains whereas the cis isomer 6a was completely inactive. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
|
