108923-79-1Relevant articles and documents
Cyclizations of Cyanothioacetamide in the Presence of Sulphur
Gewald, K.,Schindler, R.
, p. 223 - 228 (2007/10/02)
Cyanothioacetoamide 1 reacts with sulphur in the presence of triethylamine to form the 2,5-diamino-thiophene derivative 3 and in the presence of sodium ethoxide the 1,4-dihydropyridine derivative 2, respectively. 3 easily undergoes ring opening to yield the butadiene derivative 6.Catalyzed by amine from 1, cyclic ketones, and sulphur the 2-spiropyrimidine-4-thiones> 8 arise.Analogously to other cyanoacetic acid derivatives 1 react with sulphur and isothiocyanates to form the 4-amino-Δ4-thiazoline-2-thiones 9 and with sulphur and carbon disulfide to yield the 5-amino-1,2-dithiol-3-thione derivative 12.Among the o-amino-thiocarboxamides 3, 9, 12 the compounds 3 and 9 can be converted into the 5,6-heterocondensed pyrimidine-4-thiones 4 and 10.