130089-88-2Relevant academic research and scientific papers
Synthesis of substituted 1,3-cyclohexadienes, pyridine-2(1H)-thiones, and thieno[2,3-d]pyrimidine- 4(3H)-thiones by the Michael reaction
Dyachenko,Dyachenko,Chernega
, p. 397 - 406 (2007/10/03)
Cyclopentylidene- and cyclohexylidene(cyano)acetamides reacted with malononitrile and cyano-(thioacetamide) according to the Michael pattern with exchange of the methylene components to give substituted 1-amino-2,6,6-tricyano- 1,3-cyclohexadienes and thieno[2,3-d]pyrimidine-4(3H)-thiones. Condensation of cyclopentylidene- and cyclohexylidene(cyano)acetamide with 1,3-dicarbonyl compounds afforded 4,6-di-methyl-3-cyanopyridine-2(1H)-thione and morpholinium 4-methyl-6-oxo-3-cyano-1,6-dihydropyridine-2-thiolate which were converted into substituted 2-alkylsulfanylpyridines, thieno[2,3-b]pyridines, thiazolo[3,2-a]pyridine, and 2H-[1,3]thiazino[3,2-a]pyridine.
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.
