Stereoselective synthesis, spectroscopic and X-ray crystallographic characterization of novel trans- and cis-3-methylseleno substituted monocyclic ß-lactams: Potential synthons for C-3 functionalized/bicyclic/halospiroseleno-ß-lactams of medicinal interest

New series of trans- and cis-3-methylseleno substituted β-lactams (4, 5) have been prepared from 2-methylselenoethanoic acid (2). The four-membered β-lactam ring was introduced by the condensation reaction between ketene retrieved from 2-methylselenoethanoic acid (2) and suitably substituted imines...

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Bibliographic Details
Published inInorganica Chimica Acta Vol. 477; p. 172
Main Authors Bhalla, Aman, Nagpal, Yogesh, Berry, Shiwani, Narula, Dipika, Bari, SS, Bhasin, KK, Kumar, Rajeev
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier Science Ltd 24.05.2018
Subjects
Amides
Analytical chemistry
Carbon 13
Chemical synthesis
Crystal structure
Crystallography
Imines
Mass spectrometry
NMR
Nuclear magnetic resonance
Refluxing
Single crystals
Spectrum analysis
Stereoselectivity
Substitutes
Toluene
Triethylamine
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Summary:New series of trans- and cis-3-methylseleno substituted β-lactams (4, 5) have been prepared from 2-methylselenoethanoic acid (2). The four-membered β-lactam ring was introduced by the condensation reaction between ketene retrieved from 2-methylselenoethanoic acid (2) and suitably substituted imines (3a-f) in the presence of triethylamine using POCl3 in refluxing toluene. The structural and stereochemical analysis of novel trans- and cis-3-methylseleno substituted β-lactams were carried out using IR, NMR (1H and 13C), 2D-NMR (1H–1H COSY, 1H–13C HSQC), elemental analysis (CHN) and mass spectrometry (EIMS). Further, the structures of trans-1-(4′-methoxyphenyl)-3-methylseleno-4-(4′-chlorophenyl)azetidin-2-one (4b), trans-1-(4′-methoxyphenyl)-3-methylseleno-4-(4′-methylphenyl)azetidin-2-one (4c), trans- and cis-1-(4′-methoxyphenyl)-3-methylseleno-4-styrylazetidin-2-ones (4e and 5e) were established by single crystal X-ray crystallographic studies. The cis or trans configuration of the hydrogen at C-3 was assigned with respect to C4-H.
ISSN:0020-1693
1873-3255