Syntheses and Crystal Structures of Three Electron Poor N-Vinyltheophylline Derivatives |
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| Authors: | Ali Ramazani Azam Farshadi Amir Mahyari Katarzyna ?lepokura Tadeusz Lis Morteza Rouhani |
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| Affiliation: | (1) Chemistry Department, Zanjan University, PO Box 45195-313, Zanjan, Iran;(2) Faculty of Chemistry, University of Wrocław, 14 Joliot-Curie Street, 50-383 Wrocław, Poland;(3) Young Researchers Club, Zanjan Branch, Islamic Azad University, Zanjan, Iran |
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| Abstract: | 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. |
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