Collect. Czech. Chem. Commun. 1990, 55, 2722-2730

4-(5-Phenyl-1,3,4-oxadiazol-2-yl)biphenyl-4'-carboxylic acid: Its functional derivatives and their heterocyclization into 1,3-thiazine-6-thiones

Antonín Kurfürsta, Josef Kuthana, Pavel Lhotáka, Petr Nádeníka, Werner Schrothb and Roland Spitznerb

a Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czechoslovakia
b Sektion Chemie, Martin-Luther-Universität, Halle-Wittenberg, BRD


The title carboxylic acid II prepared by hypobromide oxidation of 4'-acetyl derivative I was converted into its functional derivatives III-IX by standard preparative procedures. The C-acylation of 1,1-dichloroethene with acyl chloride III gave dichloroethenyl ketone X affording 2,4-disubstituted 1,3-thiazine-6-thiones XIa-XIe and XII by cyclocondensations with appropriate thioamides. The reactivity of heterocycles XIb, XIc was checked by their conversion into the expected products XIII-XV. IR and NMR spectroscopic patterns of the new prepared compounds are discussed.