Elsevier, Tetrahedron, 47(69), p. 10014-10021, 2013
DOI: 10.1016/j.tet.2013.09.063
Full text: Unavailable
New and efficient methods for the synthesis of N1-substituted and C6-substitued adenines were developed from the easily accessible 5-aminoimidazole-4-carboxamidines. Condensation of these compounds with triethyl orthoformate led to the selective synthesis of the N1-substituted adenines. Regioselective preparation of C6-substituted adenines could be accomplished when the same precursors were combined with dimethylformamide diethyl acetal. These C6-substituted adenines could also be obtained from the N1-substituted adenines by Dimroth rearrangement in the presence of dimethyl amine.