Design and synthesis of a new class of indeno[1,2-b]pyridine thioglycosides.

This research reports a novel method for synthesizing a new class of indeno[1,2-b]pyridine thioglycosides. This series of indenopyridine thioglycosides was designed by the reaction of (E)-2-cyano-3-(furan/or thiophene-2-yl)prop-2-enethioamide 1a or 1b with 1-indanone 2 to give the corresponding 2-thiooxo-1H-indeno[1,2-b]pyridine-3-carbonitriles 3a,b. The latter compounds were treated with peracetylated sugar bromides 5 in KOH-acetone to give the corresponding indenopyridine thioglycosides 6a-h. Ammonolysis of the protected indenopyridine thioglycosides 6a-h gave the corresponding free indenopyridine thioglycosides 7a-h. The compounds have been characterized by 13C NMR, 1H NMR and IR spectra.