A new synthesis of inosine from 5-amino-1-beta-D-ribofuranosyl-4-imidazole-carboxamide.
Inosine was prepared (15% yield) by treatment of 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide (AICA-riboside) with chloroform in the presence of sodium methoxide. This ring closure can be reasonably explained by assuming the formation of dichlorocarbene from chloroform and alkali. Carbon tetrachloride or hexachloroethane as a carbene source was more effective for the ring closure of AICA-riboside, giving inosine in 48% and 51% yields respectively.
D003500:Cyclization; D007093:Imidazoles; D007288:Inosine / Q000138:chemical synthesis*; D008722:Methods; D012263:Ribonucleosides
D007093:Imidazoles; D012263:Ribonucleosides; D007288:Inosine