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

B. V. Subba Reddy; Nilanjan Majumder; T. Prabhakar Rao

doi:10.1055/s-0034-1379031

Synthesis, Table of Contents

Synthesis 2014; 46(24): 3408-3414
DOI: 10.1055/s-0034-1379031

paper

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

B. V. Subba Reddy*

^aNatural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27160512 Email: basireddy@iict.res.in

,

Nilanjan Majumder

^aNatural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27160512 Email: basireddy@iict.res.in

,

T. Prabhakar Rao

^bCenter for Nuclear Magnetic Resonance Spectroscopy, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India

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Abstract

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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-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.

Key words

Ugi four-component reaction - bifunctional substrates - sugar azidoaldehyde - isonitriles - triazolo[1,5-a][1,4]diazepines

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References

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