Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, The University of Michigan, Ann Arbor, MI 48109-1065 U.S.A.
Abstract:
1-Methylisoguanosine was synthesized by a one-pot reaction involving a condensation of 5-amino-1-(β--ribofuranosyl)imidazole-4-carboxamide (1) with methyl isothiocyanate, treatment of the resulting thiourea derivative with DCC furnished 5-(3-methyl-1-ureido)-1-(β--ribofuranosyl)imidazole-4-carbonitrile (4) which was then annulated with ethanolic ammonia to furnish doridosine in a 68% yield from 1.