ChemInform Abstract: 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.

Abstract

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-4 H -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.