Yadav, J. S. ; Subba Reddy, B. V. ; Hara Gopal, A. V. ; Nageshwar Rao, R. ; Somaiah, R. ; Purushotham Reddy, P. ; Kunwar, A. C. (2010) Domino Knoevenagel-hetero-Diels-Alder reactions: a stereoselective synthesis of sugar-annulated furo[3,2-b] pyrano[4,3-d]pyran derivatives Tetrahedron Letters, 51 (17). pp. 2305-2308. ISSN 0040-4039
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2010.02.132
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Domino Knoevenagel-hetero-Diels-Alder Reaction; 1,3-diones; Pyrazolones; Sugar Aldehyde; Polycyclic Heterocycles |
| ID Code: | 59585 |
| Deposited On: | 07 Sep 2011 05:58 |
| Last Modified: | 07 Sep 2011 05:58 |
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