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Vol. 29 No. 12 (2017): Vol 29 Issue 12

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Synthesis of Novel 4-Halomethyl-1,3-oxaselenolane Substituted Spirocyclic Azetidin-2-ones from cis-3-Allyloxy-3-benzylselenoazetidin-2-ones

https://doi.org/10.14233/ajchem.2017.20673
Dipika Narula
Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh-160 014, India
Shamsher S. Bari
Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh-160 014, India
Bimal K. Banik
Community Health System of South Texas, Edinburg, Texas 78539, USA
Aman Bhalla
Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh-160 014, India

Corresponding Author(s) : Aman Bhalla

amanbhalla@pu.ac.in

Asian Journal of Chemistry, Vol. 29 No. 12 (2017): Vol 29 Issue 12

Abstract

A mild and efficient synthetic approach for the synthesis of novel 4-halomethyl-1,3-oxaselenolane substituted spirocyclic b-lactams via intraselenyl cyclization of cis-3-allyloxy-3-benzylselenoazetidin-2-one mediated by halogens (I2, Br2) is described. The mechanism involves step-wise electrophilic addition-dealkylation sequence generating spiroseleno-b-lactams stereospecifically. The novel synthesized b-lactams have been characterized by spectroscopic techniques viz. NMR (1H, 13C, 77Se), FT-IR and elemental analysis. The cis configuration of the nucleophilic substituent at C-3 was assigned with respect to C4-H. Intraselenyl cyclization is a novel approach in the chemistry of b-lactam research.

Keywords

Spirocyclic Azetidin-2-ones Nucleophile Intraselenyl Cyclization 1,3-Oxaselenolane Lewis acid
Narula, D., Bari, S. S., Banik, B. K., & Bhalla, A. (2017). Synthesis of Novel 4-Halomethyl-1,3-oxaselenolane Substituted Spirocyclic Azetidin-2-ones from cis-3-Allyloxy-3-benzylselenoazetidin-2-ones. Asian Journal of Chemistry, 29(12), 2582–2586. https://doi.org/10.14233/ajchem.2017.20673
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