Domino Knoevenagel-hetero-Diels-Alder reactions: a stereoselective synthesis of sugar-annulated furo[3,2-b] pyrano[4,3-d]pyran derivatives |
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| Authors: | J.S. Yadav B.V. Subba Reddy R. Nageshwar Rao P. Purushotham Reddy |
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| Affiliation: | a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
b Center for Nuclear Magnetic Resonance, Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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| Abstract: | The O-propargyl derivative of a sugar aldehyde derived from d-glucose undergoes smooth intramolecular domino Knoevenagel-hetero-Diels-Alder reactions with 1,3-diketones in the presence of CuI/Et3N system in refluxing methanol to afford a novel class of carbohydrate analogues, furopyranopyrans in good yields. 1-Aryl-pyrazol-5-ones also undergo smooth coupling with O-propargyl tethered sugar aldehyde under similar conditions to furnish pyrazole-annulated furopyranopyrans. The stereochemistry of the products was assigned by various NMR experiments. |
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| Keywords: | Domino Knoevenagel-hetero-Diels boldFont" >-Alder reaction 1,3-Diones Pyrazolones Sugar aldehyde Polycyclic heterocycles |
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