Microwave-Assisted Preparation of N-Alkylated Saccharins and Their Reactions with Potassium t-Butoxide

Abstract

A simple and efficient method of N-alkylation, using either conventional heating or microwave irradiation, was applied successfully to the alkylation of several substituted saccharins. Subsequent t-butoxide-induced condensation of these products led to the formation of fused polycyclic sultams, which could be a privileged framework in the field of medicinal chemistry because of their favorable hydrophilic nature and straightforward functionalization.

Keywords:

• Condensation
• microwave-assisted alkylation
• polycyclic sultam
• saccharin

ACKNOWLEDGMENTS

This work was supported financially by the Slovenian Research Agency. The authors thank Professor Roger Pain for his critical reading of the manuscript.

Notes

Notes. Method A: conventional heating for 3 h at 140 °C. Method B: microwave irradiation for 15 min at 100 °C.

^a In the syntheses of 3a and 3b, the reagent 1 used was sodium saccharin. In those cases, the use of K₂CO₃ was not needed.