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An efficient synthesis of spiro- β-lactams having sulfenyl, sulfinyl and sulfonyl moiety

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Abstract

An efficient and a facile route to spiro- β-lactams is described. 3-allyl-3-methylthio- β-lactams, which are synthesized through a Lewis acid mediated C-3 alkylation of the trans-3-chloro-3-methylthio- β-lactams, undergo a facile intrasulfenyl cyclization reaction in the presence of halogens like bromine and iodine to give spiro β-lactams in good yield. These halospiro- β-lactams are then subjected to dehalogenation reaction using Raney-nickel. The resulting spiro- β-lactams are further transformed into their sulfinyl and sulfonyl derivatives by using m-chloroperbenzoic acid as an oxidant.

A facile synthesis of novel sulfinyl and sulfonyl spiro-β-lactams through intramolecular cyclization of cis-3-allyl-3-methylthio-β-lactams is described.

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Acknowledgement

We gratefully acknowledge the financial support for this work from Council of Scientific and Industrial Research (CSIR), New Delhi, India.

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Authors and Affiliations

  1. D. A. V. College, Sector 10, Chandigarh, India

    RESHMA

  2. University Institute of Engineering and Technology, Panjab University, Chandigarh, India

    RENU ARORA

  3. Department of Chemistry, Guru Nanak Dev University, Amritsar, India

    GEETA HUNDAL

  4. Department of Chemistry and Centre of Advanced studies in Chemistry, Panjab University, Chandigarh, 160014, India

    AMAN BHALLA & S S BARI

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  1. RESHMA
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  2. RENU ARORA
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Correspondence to S S BARI.

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Supplementary Information

All additional information pertaining to characterization of the representative compounds (4d, 5d, 8c, 9b, 10b, 11b) using 1H NMR and 13C NMR technique (Figures S1-S5) are given in the supporting information. Supplementary Information is available at www.ias.ac.in/chemsci.

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RESHMA, ARORA, R., HUNDAL, G. et al. An efficient synthesis of spiro- β-lactams having sulfenyl, sulfinyl and sulfonyl moiety. J Chem Sci 127, 1957–1966 (2015). https://doi.org/10.1007/s12039-015-0956-1

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  • DOI: https://doi.org/10.1007/s12039-015-0956-1

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