Asymmetric one-pot synthesis of cyclopropanes

Naoufel Ben Hamadi, Ahlem Guesmi, Wided Nouira

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).


Keywords


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

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DOI: http://dx.doi.org/10.20450/mjcce.2016.835

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