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Synthesis and antimicrobial activity of fatty 2-morpholinones prepared from epoxy fatty acid methyl esters

  • Technical
  • Published:
Journal of the American Oil Chemists Society

Abstract

Reactions of methyl 10,11-epoxyundecanoate (I), methyl 9,10-epoxyoctadecanoate (II) methyl 12,13-epoxy-cis-9-octadecenoate (III) and methyltrans-2,3-epoxyhexadecenoate (IV) with glycine in dimethylformamide (DMF) in the presence of anhydrous AlCl3 as catalyst have yielded 5(6)-[8′-carbomethoxyoctyl]-2-morpholinone (V); 5(6)-[7′'-carbomethoxyheptyl]-6(5)-octyl-2-morpholinone (VI);5(6)-[10′-carbomethoxydec-cis-2-enyl)-6(5)-pentyl-2-morpholinone (VII), and 5-tridecyl-6-carbomethoxy 2-morpholinone (VIII), respectively in excellent yield. The products have been characterized with the help of spectral data and microanalysis. Antifungal and antibacterial screening of (V–VIII) showed pronounced activity against four bacteria and seven fungal species.

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Authors and Affiliations

  1. Section of Oils and Fats, Department of Chemistry, Aligarh Muslim University, 2O2 OO2, Aligarh, India

    R. Agarwal, M. H. Ansari, M. W. Y. Khan & M. Ahmad

  2. Mycology Research Laboratory, Agra College, Uttar Pradesh, India

    K. D. Sharma

Authors
  1. R. Agarwal
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  2. M. H. Ansari
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  3. M. W. Y. Khan
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  4. M. Ahmad
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  5. K. D. Sharma
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Agarwal, R., Ansari, M.H., Khan, M.W.Y. et al. Synthesis and antimicrobial activity of fatty 2-morpholinones prepared from epoxy fatty acid methyl esters. J Am Oil Chem Soc 66, 825–827 (1989). https://doi.org/10.1007/BF02653677

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  • DOI: https://doi.org/10.1007/BF02653677

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