Four-Component, One-Pot Synthesis of N-Alkyl-4-oxo-3-phenylhexahydro-4H-spiro{[1,3]dioxolo[4′, 5′: 4,5]furo[2,3-f][1,2,3]triazolo[1,5-a][1,4]diazepine-9,1′- cyclohexane}-6-carboxamide Derivatives

A four-component, six-center Ugi reaction of sugar azidoaldehyde, benzylamine, alkyl isocyanide, and phenylpropiolic acid has been developed to produce a novel class of hexahydro-4H-spiro{[1,3]dioxolo[4,5:4,5]furo[2,3-f][1,2,3]triazolo[1,5-a][1,4]diazepine-9,1-cyclohexane}-6-carboxamide derivatives in good yields with high selectivity. It is a one-pot two-step process affording sugar-derived triazolodiazepines starting from simple precursors. The stereochemistry of the products was confirmed by NMR and NOE studies.