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 C~12~ bis(tetrazole) 6 was prepared and represents a valuable supplement to the previously known C~2~−C~5~ alkyl‐ and alkenyl‐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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)