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Journal of Chemical Crystallography

, Volume 41, Issue 9, pp 1376–1385 | Cite as

Syntheses and Crystal Structures of Three Electron Poor N-Vinyltheophylline Derivatives

  • Ali Ramazani
  • Azam Farshadi
  • Amir Mahyari
  • Katarzyna Ślepokura
  • Tadeusz Lis
  • Morteza Rouhani
Original Paper

Abstract

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and alkyl acetylenecarboxylates (or dialkyl acetylenedicarboxylates) by theophylline leads to vinyltriphenylphosphonium salts, which undergo Michael addition reaction with conjugate base to produce phosphorus ylides. Silica gel was found to catalyze conversion of the phosphorus ylides to electron-poor N-vinyl imidazoles in solvent-free conditions under thermal (90 °C, 1 h) conditions. The structures of these compounds were confirmed by IR, 1H, and 13C NMR spectroscopy, and single crystal X-ray structure determination. The structural analysis of the products indicated that the reaction is completely regio- and stereoselective.

Graphical Abstract

The syntheses of titled compounds were achieved in one pot using alkyl acetylenecarboxylates (or dialkyl acetylenedicarboxylates), triphenylphosphine and theophylline in the presence of a catalytic amount of silica gel. The structures of these compounds were confirmed by IR, 1H, and 13C NMR spectroscopy, and single crystal X-ray structure determination. X-ray crystal studies were undertaken for three compounds and the results are presented. The structural analysis of the products indicated that the reaction is completely regio- and stereoselective.

Keywords

Silica gel Theophylline Acetylenic esters Vinyltriphenylphosphonium salts Crystal structure N-Vinyl imidazole 

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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Ali Ramazani
    • 1
  • Azam Farshadi
    • 1
  • Amir Mahyari
    • 1
  • Katarzyna Ślepokura
    • 2
  • Tadeusz Lis
    • 2
  • Morteza Rouhani
    • 3
  1. 1.Chemistry DepartmentZanjan UniversityZanjanIran
  2. 2.Faculty of ChemistryUniversity of WrocławWrocławPoland
  3. 3.Young Researchers Club, Zanjan BranchIslamic Azad UniversityZanjanIran

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