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Synthesis and antimicrobial activity of fatty 2‐morpholinones prepared from epoxy fatty acid methyl esters
Author(s) -
Agarwal R.,
Ansari M. H.,
Khan M. W. Y.,
Ahmad M.,
Sharma K. D.
Publication year - 1989
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02653677
Subject(s) - anhydrous , chemistry , antimicrobial , fatty acid , epoxy , catalysis , antibacterial activity , methyl oleate , yield (engineering) , antifungal , dimethylformamide , fatty acid methyl ester , organic chemistry , bacteria , nuclear chemistry , microbiology and biotechnology , biology , materials science , genetics , solvent , biodiesel , metallurgy
Reactions of methyl 10,11‐epoxyundecanoate (I), methyl 9,10‐epoxyoctadecanoate (II) methyl 12,13‐epoxy‐ cis ‐9‐octadecenoate (III) and methyl trans ‐2,3‐epoxyhexadecenoate (IV) with glycine in dimethylformamide (DMF) in the presence of anhydrous AlCl 3 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.