On May 17, 1985, Hennen, William J.; Hinshaw, Barbara C.; Riley, Timothy A.; Wood, Steven G.; Robins, Roland K. published an article.Formula: C10H11N3O3S The title of the article was Synthesis of 4-substituted 5-amino-2-(β-D-ribofuranosyl)thiazoles and 4-substituted 5-amino-2-(β-D-ribofuranosyl)selenazoles, and their respective conversion into 2-(β-D-ribofuranosyl)thiazolo[5,4-d]pyrimidines and 2-(β-D-ribofuranosyl)selenazolo[5,4-d]pyrimidines. A new synthesis of tiazofurin and selenazofurin. And the article contained the following:
Anhydroallonothioate (I; Z = S) and -selenoate (I; Z = Se), prepared by treatment of anhydroallonimidate (I; Z = NH) with H2S and H2Se, underwent cyclocondensation with H2NCH(CN)2, NCCN(NH2)CONH2, or NCCH(NH2)CO2Et to give C-nucleosides II (X = S, R = NH2, R1 = cyano; X = S, Se, R = NH2, R1 = CONH2; X = S, Se, R = NH2, R1 = CO2Et). II (X = S, R = NH2, R1 = cyano; X = S, Se, R = NH2, R1 = CONH2) were further cyclized with H2NCH:NH or HC(OEt)3 to give thiazolo- and selenazolopyrimidine C-nucleosides, e.g., III (X = S, Se). II (X = S, Se, R = NH2, R1 = CO2Et) were converted in 2 steps into tiazofurin and selenazofurin (II; X = S, Se, R = H, R1 = CONH2), resp. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Formula: C10H11N3O3S
The Article related to aminoribofuranosylthiazole, aminoribofuranosylselanazole, thiazole c nucleoside, selenazole c nucleoside, ribofuranosylthiazolopyrimidine, ribofuranosylselenazolopyrimidine, thiazolopyrimidine ribofuranosyl, selenazolopyrimidine ribofuranosyl, tiazofurin, selenazofurin, nucleoside c thiazole selenazole and other aspects.Formula: C10H11N3O3S
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts