Synthesis of New Heterocyclic Fatty Compounds

Sandra Fuermeier et.al.: Synthesis of New Heterocyclic Fatty Compounds

Author(s): Sandra Fuermeier, Juergen O. Metzger

Title: Synthesis of New Heterocyclic Fatty Compounds

Date of Upload: 2003

Article: Eur. J. Org. Chem. 2003, 885-893, Department of Chemistry, University of Oldenburg, Carl-von-Ossietzky-Str. 9-11, 26129 Oldenburg, Germany

Keywords: Fatty acids, Nitrogen heterocycles, Oxygen heterocycles, Renewable feedstocks, sustainable development, vegetable oil, plant oil

Abstract:

The terminal tetrazoles 1−5, the tetrazole analogues of the most important naturally occurring fatty acids, have been synthesized from fatty nitriles and completely characterized. The linear C12 bis(tetrazole) 6 was prepared and represents a valuable supplement to the previously known C2−C5 alkylandalkenyl-linked bis(tetrazoles). The tetrazoles 1−6 were converted into the respective 1,3,4-oxadiazoles 13−17 by heating in acetic anhydride. Three bis(oxadiazoles) 18−20 were also obtained. A 1,5-disubstituted tetrazole 12 was synthesized from methyl 9(10)-oxooctadecanoate by means of an improved Schmidt reaction. From methyl cis-9,10-epoxyoctadecanoate(21), various heterocycles such as the 4,5-dihydrooxazoles 22, the oxazolidines 24, the imidazoles 26, the oxazoles 27, and the imidazolinethione 28 were prepared. Because of their structural relationship to the naturally occurring prostaglandins, compounds 12, 22, 24, 26, 27, and 28 should be of interest as homoprostanoids.

URL: http://www.chemie.uni-oldenburg.de/oc/metzger/publikationen/pdf/95.pdf (application/pdf)

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