Asymmetric one-pot synthesis of cyclopropanes

Authors

  • Naoufel Ben Hamadi Al Imam Mohammad Ibn Saud Islamic University (IMSIU), College of Sciences, Department of Chemistry, 11623 Riyadh http://orcid.org/0000-0002-2410-5275
  • Ahlem Guesmi Al Imam Mohammad Ibn Saud Islamic University (IMSIU), College of Sciences, Department of Chemistry, 11623 Riyadh
  • Wided Nouira Laboratory of Interfaces and Advanced Materials, University of Monastir, Avenue of Environment, 5019 Monastir

DOI:

https://doi.org/10.20450/mjcce.2016.835

Keywords:

1, 3-dipolar cycloaddition, aromatic nitrile oxides, propargyl O-glycoside, isoxazole.

Abstract

Cycloaddition of the diazoalkanes to electron-deficient olefins (in situ) affords polysubstituted cyclopropanes in high yields (up to 85%). Deprotection of the ketal protecting group provided water-soluble cyclopropane-bearing carbohydrate in good yields. Antimicrobial activity screening of the synthesized compounds 8 and 9, utilizing a variety of Gram-positive (Staphylococcus aureus and Enterococcus fecalis), Gram-negative bacteria (Escherichia coli and Klebsiella pneumoniae) and yeast (Candida albicans), exhibited that all the prepared analogues acquire promising activities against both Gram-positive and Gram-negative bacteria especially compounds 9b and 9c (antimicrobial active agents against Gram-negative bacteria).

Author Biography

Ahlem Guesmi, Al Imam Mohammad Ibn Saud Islamic University (IMSIU), College of Sciences, Department of Chemistry, 11623 Riyadh

chemistry

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Published

2016-04-18

How to Cite

Ben Hamadi, N., Guesmi, A., & Nouira, W. (2016). Asymmetric one-pot synthesis of cyclopropanes. Macedonian Journal of Chemistry and Chemical Engineering, 35(1), 45–52. https://doi.org/10.20450/mjcce.2016.835

Issue

Vol. 35 No. 1 (2016)

Section

Organic Chemistry

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