Seleno-β-lactams: synthesis of monocyclic and spirocyclic selenoazetidin-2-ones |
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Authors: | Aman Bhalla |
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Institution: | Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh 160014, India |
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Abstract: | An efficient protocol for the synthesis of novel seleno-β-lactams using operationally simple strategies is presented. 3-Phenyl/benzylseleno-β-lactams, obtained from 2-phenyl/benzylselenoethanoic acids, are transformed to cis-3-chloro-3-phenyl/benzylseleno-β-lactams, which undergo reaction with various active aliphatic and aromatic substrates catalyzed by Lewis acid to produce cis-3-alkoxy-3-phenyl/benzylseleno-β-lactams and C-3 monosubstituted seleno-β-lactams. Halogen mediated intraselenyl cyclization of cis-3-(prop-2-ynyloxy)-3-benzylseleno-β-lactams affords novel spiro seleno-β-lactams. |
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Keywords: | Seleno-β-lactam Selenoazetidin-2-one Lewis acid Nucleophile Alkoxyseleno-β-lactam Monosubstituted seleno-β-lactam Spiro seleno-β-lactam |
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