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Serendipitous discovery of a regioselective synthesis of novel benzoyloxy substituted phenyl/benzyl-sulfanyl/selenylbisesters, 3-benzoyloxy-3-(phenylsulfanyl)-β-lactams and their antimicrobial evaluation.
- Source :
- Journal of Sulfur Chemistry; Dec2023, Vol. 44 Issue 6, p712-732, 21p
- Publication Year :
- 2023
-
Abstract
- 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, <superscript>1</superscript>H NMR, <superscript>13</superscript>C 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]
- Subjects :
- LACTAMS
BENZOYL peroxide
ELEMENTAL analysis
COPPER
ISOMERS
ANTI-infective agents
Subjects
Details
- Language :
- English
- ISSN :
- 17415993
- Volume :
- 44
- Issue :
- 6
- Database :
- Complementary Index
- Journal :
- Journal of Sulfur Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 173469072
- Full Text :
- https://doi.org/10.1080/17415993.2023.2233652