A concise pathway to synthesize a novel class of pyrido(2,3-d)pyrimidine-C-β-d-glycosides

A concise pathway to synthesize a novel class of nine different pyrido(2,3-d)pyrimidine-C-β-d-glycosides is reported. Formation of Michael adduct as an intermediate followed by heterocyclization are the key steps and the products were characterized by different spectral studies. β-Anomeric forms of C-glycosides were assigned from 1H NMR spectroscopy.

Graphical abstractA concise pathway to synthesize a novel class of nine different pyrido (2,3-d)pyrimidine-C-β-d-glycosides is reported. Formation of Michael adduct as an intermediate followed by heterocyclization are the key steps and the products were characterized by different spectral studies. β-Anomeric forms of C-glycosides were assigned from 1H NMR spectroscopyFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Synthesis of glycosidic ketones. ► Synthesis of α-,β-unsaturated-β-C-glycosidic ketones. ► Synthesis of pyrido(2,3-d)pyrimidine-C-β-d-glycosides involving the formation of Michael adduct followed by heterocyclization. ► Optimization of experimental conditions. ► Assignment of β-anomeric forms of C-glycosidic products by 1H NMR spectral studies.