Some studies in nitrogen heterocyclic chemistry using Reissert compounds

The thesis reports the first examples of Reissert compounds prepared from five-membered ring heterocycles. The method utilises trimethylsilyl cyanide as the key reagent in a single phase non-aqueous medium. Previous attempts to synthesise such compounds have failed because, under the conventional two phase conditions, the reaction either does not proceed or ring opening of the heterocycle occurs. Reaction of benzothiazole with an acid chloride (aliphatic, aromatic or chloroformate) and trimethylsilyl cyanide in dichloromethane has been shown to give rise to 3-acyl-2-cyano-2,3-dihydrobenzothiazoles. Eight such five-membered ring Reissert compounds have been prepared, mostly in yields exceeding 70%. The mechanistic involvement of trimethylsilyl cyanide is discussed. The novel Reissert compounds have been shown to be versatile intermediates for the further modification of the starting heterocycles. [Continues.]