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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 17, 1987 - Issue 4
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Original Articles

Facile, One-Step Preparation of Trigonellinate Esters

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Pages 451-455 | Published online: 05 Dec 2006

References

  • Bodor , N. , Farag , H. and Brewster , M. E. 1981 . Science , 214 : 1370
  • Bodor , N. and Brewster , M. E. 1983 . Pharmacol. Ther. , 19 : 337
  • Bodor , N. and Farag , H. 1983 . J. Med. Chem. , 26 : 313
  • Bodor , N. , McCornack , J. and Brewster , M. E. 1986 . Int. J. Pharm. , in print
  • Nuvole , A. , Paglich , G. , Sanna , P. and Acheson , R. M. 1984 . J. Chem. Res.(S) , : 356
  • Tedjamulia , M. , Srivastava , P. and Knapp , F. 1985 . J. Med. Chem. , 28 : 1574
  • Bailey , D. , Winwood , D. and Bodor , N. (unpublished results)
  • A mixture of nicotinic anhydride 3.5 g (0.015 mole) and methyl iodide 5.44 g (0.0383 mole) was refluxed in acetonitrile overnight. The orange crystals formed were fi1tered and washed with dry ether. Yield 85%. M. P. 213–215°C. 1H NMR (d6-DMSO) δ pyridine protons 8.03–9.36 (multiplet), methyl protons 4.45 (singlet). IR (KBr) -CH3 stretch broad, 2800–3200 cm−1), anhydride stretch (1750, 1810 cm−1). Anal, calculated for C14H14N2O3I2. C, 32.81; H, 2.73; N, 5.47; I, 49.61. Found: (C, 32.66; R, 2.59; N, 5.60, I, 49.66
  • 1H NMR (d6-DMSO) δ pyridine protons 8.12–9.48 (multiplet), purine C8proton 7.93 (singlet), purine C3-NH2 6.51 (broad singlet) -CH2O- 5.45 (singlet), N+-CH3 4.51 (singlet), -CH2-(C[dbnd]O)O 3.84–8.06 (multiplet), O-CH2 3.42–3.51 (multiplet)

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