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2-(2`,3`,5`-Tri-O-acetyl-b-D-ribofuranosyl)-4-(p-tolylazo)-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.
Molbank 2003, 2003(1), M306; https://doi.org/10.3390/M306
Submission received: 16 June 2002 / Accepted: 30 September 2002 / Published: 11 March 2003
Molbank 2003 m306 i001
To a solution of 4-(4-methylphenylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one (1) [1] (0.81g, 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 any remaining traces of HMDS. To a solution of the residue in anhydrous 1,2-dichloroethane (25 ml) was added 1,2,3,5-tetra-O-acetyl-b-D-ribofuranose (0.954g, 3 mmol). The mixture was treated with SnCl4 (1.1mmol) [2,3] and was then stirred at room temperature for two hours and followed by 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 methylene chloride / methanol (98:2 v/v) to give 1.3 g (82%) of 3 as orange powder.
Rf: 0.253 (methylene chloride / methanol, 98 : 2 v/v).
UV (lmax , 95% ethanol): 384 nm
IR (KBr, cm-1): 1747 (CO ester), 1674 (CO Pyrazolone).
MS (m/z): 528.
1H-NMR (250 MHz, CDCl3): 2.10 (s, 9H, COCH3); 2.31 (s, 3H, CH3); 2.42 (s, 1H, CH); 4.14-4.19 (dd, 1H, H-5`); 4.32-4.37 (m, 1H, H-4`); 4.43-4.48 (dd, 1H, H-5``); 5.56 (t, 1H, H-3`, J3`,4`=5.49 Hz); 5.72 (t, 1H, H-2`, J2`,3`=5.31 Hz); 6.03 (d, 1H, H-1`, J1`,2`=4.2 Hz); 7.23 (dd, 4H, aromatic CH).
13C-NMR (75 MHz, CDCl3): 21.9 (CH3); 48.5 (CH); 63.0 (C-5`), 70.84 (C-3`); 72.7 (C-2`); 79.7 (C-4`); 84.4 (C-1`); 116.9 (2 aromatic carbons), 121.1, 122.0 (2 aromatic carbons), 130.5, 144.1 (2 quaternary aromatic carbons); 137.5 (q, CF3); 149.2 (C=N); 169.5, 169.8, 170.7, 173.0 (4 CO).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References and Notes

  1. Zohdi, H. F.; Rateb, N. M. Molbank 2003, M305.
  2. Vorbruggen, H.; Bennua, B. Chem. Ber. 1981, 114, 1279.
  3. Haikal, A.; Zohdi, H. F.; El-Neyadi, S. Molecules 2001, 6, M262.
  • Sample Availability: Available from the authors and from MDPI

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MDPI and ACS Style

Haikal, A.; Zohdi, H.F.; Badi, Z. 2-(2`,3`,5`-Tri-O-acetyl-b-D-ribofuranosyl)-4-(p-tolylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one. Molbank 2003, 2003, M306. https://doi.org/10.3390/M306

AMA Style

Haikal A, Zohdi HF, Badi Z. 2-(2`,3`,5`-Tri-O-acetyl-b-D-ribofuranosyl)-4-(p-tolylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one. Molbank. 2003; 2003(1):M306. https://doi.org/10.3390/M306

Chicago/Turabian Style

Haikal, Abdelfattah, Hussein F. Zohdi, and Zahra Badi. 2003. "2-(2`,3`,5`-Tri-O-acetyl-b-D-ribofuranosyl)-4-(p-tolylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one" Molbank 2003, no. 1: M306. https://doi.org/10.3390/M306

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