Multicomponent one pot synthesis of C-glucosides of 1-azaindolizines

Abstract

A protocol based on Groebke-Blackburn-Bienayame (GBB) multicomponent reaction has been developed for efficient and atom economical synthesis of C-glucosides of 1-azaindolizine, i.e. 2-(β-D-glucopyranosyl)-3-N-alkylamino-1-azaindolizine. Thus, a series of fourteen novel 2-(β-D-glucopyranosyl)-3-N-alkylamino-1-azaindolizines have been synthesized in moderate to good yields by reaction of a perbenzylated β-C-glucopyranosyl aldehyde with differently substituted 2-aminopyridines and alkyl isocyanides using InCl₃ as acid catalyst. All synthesized β-C-glucosides were unambiguously characterized with the help of spectroscopic (IR, ¹H-NMR, ¹³C-NMR and mass spectra) data analysis.

Graphical Abstract

Keywords:

• β-C-glucopyranosyl aldehyde
• C-glucosides of 1-azaindolidines
• 2-(β-D-glucopyranosyl)-3-N-alkylamino-1-azaindolizines
• multicomponent reaction
• perbenzylated

Acknowledgments

We are thankful to CIF-USIC, University of Delhi, for providing the NMR spectral and HRMS recording facility.