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Experimental and theoretical investigation of benzyl-N-pyrrolylketene, one- step procedure for preparing of new β-lactams by [2 +2] cycloaddition reaction

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Abstract

3-Phenyl-2-(1-H-pyrrol-1-yl) propanoic acid has been used as a ketene source in synthesizing of monocyclic-2-azetidinones. Hindrance in ketene and imines successfully controlled the diastereoselectivity of the reaction. For example, in some cases only one isomer was achieved. By using Mukaiyama reagent, the leaving group in acid was activated and the by-products were separated by simple aqueous work-up. DFT calculation indicated that the benzyl-N-pyrrolylketene has nonconjugated structure and the pyrrolyl ring is perpendicular to the ketene plane in both the twisted and planar structures.

3-Phenyl-2-(1-H-pyrrol-1-yl) propanoic acid as a ketene source has been used in synthesizing of monocyclic-2-azetidinones. Hindrance in ketene and imines successfully controlled the diastereoselectivity. DFT calculation indicated that benzyl-N-pyrrolylketene has unconjugated structure and the pyrrolyl ring is perpendicular to the ketene plane in both twisted and planner structures.

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Acknowledgements

This work was supported by grants from the Research Council of Shahid Bahonar University of Kerman.

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  1. Department of Chemistry, Shahid Bahonar University of Kerman, Kerman, 76169-14111, Iran

    MASOUMEH BEHZADI, KAZEM SAIDI, MOHAMMAD REZA ISLAMI & HOJATOLLAH KHABAZZADEH

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  1. MASOUMEH BEHZADI
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  2. KAZEM SAIDI
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  3. MOHAMMAD REZA ISLAMI
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Correspondence to KAZEM SAIDI.

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Supplementary Information

Copies of IR, 1H NMR, 13C NMR and Mass spectra for a representative set of compounds 6a-j and NOE-difference experiments for 6d-e, are available at www.ias.ac.in/chemsci.

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BEHZADI, M., SAIDI, K., ISLAMI, M.R. et al. Experimental and theoretical investigation of benzyl-N-pyrrolylketene, one- step procedure for preparing of new β-lactams by [2 +2] cycloaddition reaction. J Chem Sci 128, 111–117 (2016). https://doi.org/10.1007/s12039-015-1007-7

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