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 - Concepedia

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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

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References

2014

Year

B. V. Subba Reddy, Nilanjan Majumder, T. Venkateswara Rao

Diversity Oriented SynthesisDerivativesBiochemistrySugar AzidoaldehydeNatural SciencesDiversity-oriented SynthesisOne-pot SynthesisOrganic ChemistrySimple PrecursorsStereoselective SynthesisSix-center Ugi ReactionHeterocycle ChemistryPharmacology

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<i>H</i>-spiro{[1,3]dioxolo[4′,5′:4,5]furo[2,3-<i>f</i>][1,2,3]triazolo[1,5-<i>a</i>][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.