Collect. Czech. Chem. Commun. 1986, 51, 112-117

Synthesis of isothiocyanates from non-aromatic nitrogen-containing heterocycles

Jozef Gonda, Pavol Kristian and Ľubomír Mikler

Department of Organic Chemistry and Biochemistry, Šafárik University, 041 67 Košice


Investigation of the reaction of thiophosgene with Δ2-oxazolines I, Δ3-thiazolines II, 4H-benzo[d][1,3]thiazines III, 2-methoxypentahydro-Δ1-azepine IV, theophylline and caffeine showed that only compounds I and IV reacted to give 2-acyloxyethyl isothiocyanates and methyl 6-isothiocyanatohexanoate. The structure of these products was corroborated by IR, 1H NMR, 13C NMR and mass spectral methods. The suitability of the above-mentioned compounds to react is discussed.