Cyclization reactions of N1-(glycopyranosylamino) guanidines

Article abstract of DOI:10.1016/S0008-6215(97)00116-X

Acetylation of N¹-(aldopyranosylamino)guanidines 2-4 with D-gluco, D-galacto, and L-arabino configuration gives rise to N¹-per(O-acetylglycopyranosylamino)-N¹,N²,N³-triacetylguanidines 5-7 in good yields, as already stated by Feather and coworkers [Carbohydr. Res., 267 (1995) 17-25] for the gluco compound. The acylaminoguanidines prepared have been cyclized under mild conditions (boiling in ethanol or treatment with cold 0.1 M sodium methylate solution) to afford 3-amino-N¹-glycopyranosyl-5-methyl-1H-1,2,4-triazoles. The structure of these pyranosyl nucleosides 9, 10, 12-14 is discussed using ¹H and ¹³C NMR spectroscopy and mass spectrometry.