Next Article in Journal
2-(b-D-Ribofuranosyl)-4-(3-nitrophenylazo)-5-trifluoromethyl-2,4-dihydro-pyrazol-3-one
Previous Article in Journal
4-(3-Nitrophenylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one
 
 
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

2-(2`,3`,5`-Tri-O-acetyl-b-D-ribofuranosyl)-4-(3-nitrophenylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one

Department of Chemistry, Faculty of Science, United Arab Emirates University, P.O.Box 17551 Al-Ain, UAE
*
Author to whom correspondence should be addressed.
Molecules 2001, 6(12), M262; https://doi.org/10.3390/M262
Submission received: 5 June 2001 / Accepted: 15 December 2001 / Published: 20 December 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 06 m262 i001
To a solution of 4-(3-nitrophenylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one 1 [1] (0.903 g, 3 mmol) in hexamethyldisilazine (HMDS) (25 ml) was added few crystals of anhydrous ammonium sulfate [2]. The mixture was refluxed for three hours, then it was evaporated under vacuum to dryness. The residue was mixed with anhydrous xylene (30 ml) and the resulted solution was re-evaporated under vacuum to dryness to remove the remaining traces of HMDS. To a solution of the residue in anhydrous 1,2-dichloromethane (25 ml) was added 1,2,3,5-tetra-O-acetyl-b-D-ribofuranose (0.954g, 3 mmol). The mixture was treated with SnCl4 (1.1 mmol) [2] and was then stirred at room temperature for two hours (tlc). The reaction mixture was diluted with dichloromethane (25 ml), washed with saturated aqueous solution of sodium bicarbonate (50 ml) and water (3x30 ml). The organic layer was dried over anhydrous sodium sulfate, filtered, evaporated to a small volume and chromatographed over silica gel column using ethyl acetate / n-hexane (4:6 v/v) to give 1.34g (80%) of 3 as yellow powder.
Rf (ethyl acetate/n-hexane, 50/50, v/v): 0.3.
UV (lmax, 95% ethanol): 266, 404.
MS (m/z): 559.
1H-NMR (250 MHz, CDCl3): 2.07(s, 9H, COCH3); 4.07-4.13(dd, 1H, H-5``); 4.32-4.27(m, 1H, H-4`); 4.36-4.41(dd, 1H, H-5`, J5`,4`=3.3, J5`,5``=12.27); 5.44-5.48(t, 1H, H-3`, J3`,4`=5.31); 5.62-5.65(dd, 1H, H-2`, J2`,3`=5.67); 5.95(d, 1H, H-1`, J1`,2`=3.84); 7.56-8.22(m, 4H, aromatic CH).
13C-NMR (75 MHz, CDCl3): 70.65(C-5`), 72.48(C-3`); 76.99(C-2`); 79.75(C-4`); 84.44(C-1`); 111.52, 117.81, 120.36, 122.85, 124.50, 131.11(6 aromatic carbons); 136.60(q, CF3); 142.74(C-4); 148.56(C-5); 157.68(C-3); 169.40, 169.60, 170.63(3 CO).

Supplementary Materials

References

  1. Zohdi, H.F.; Rateb, N.M.; Haikal, A. Molecules 2001, 6, M261. [CrossRef]
  2. Vorbruggen, H.; Bennua, B. Chem. Ber. 1981, 114, 1279. [CrossRef]
Sample Availability: Available from the authors.

Share and Cite

MDPI and ACS Style

Haikal, A.; Zohdi, H.F.; El-Neyadi, S. 2-(2`,3`,5`-Tri-O-acetyl-b-D-ribofuranosyl)-4-(3-nitrophenylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one. Molecules 2001, 6, M262. https://doi.org/10.3390/M262

AMA Style

Haikal A, Zohdi HF, El-Neyadi S. 2-(2`,3`,5`-Tri-O-acetyl-b-D-ribofuranosyl)-4-(3-nitrophenylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one. Molecules. 2001; 6(12):M262. https://doi.org/10.3390/M262

Chicago/Turabian Style

Haikal, Abdelfattah, Hussein F. Zohdi, and Shaikha El-Neyadi. 2001. "2-(2`,3`,5`-Tri-O-acetyl-b-D-ribofuranosyl)-4-(3-nitrophenylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one" Molecules 6, no. 12: M262. https://doi.org/10.3390/M262

Article Metrics

Back to TopTop