synthesis of new unsymmetrical 4,5-dihydroxy-2-imidazolidinones. dynamic nmr spectroscopic study of the prototropic tautomerism in 1-(2-benzimidazolyl)-3-phenyl-4,5-dihydroxy-2-imidazolidinone合成新的不对称4,5-dihydroxy-2-imidazolidinones。.pdfVIP

synthesis of new unsymmetrical 4,5-dihydroxy-2-imidazolidinones. dynamic nmr spectroscopic study of the prototropic tautomerism in 1-(2-benzimidazolyl)-3-phenyl-4,5-dihydroxy-2-imidazolidinone合成新的不对称4,5-dihydroxy-2-imidazolidinones。.pdf

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synthesis of new unsymmetrical 4,5-dihydroxy-2-imidazolidinones. dynamic nmr spectroscopic study of the prototropic tautomerism in 1-(2-benzimidazolyl)-3-phenyl-4,5-dihydroxy-2-imidazolidinone合成新的不对称4,5-dihydroxy-2-imidazolidinones。

Molecules 2006, 11, 768-775 molecules ISSN 1420-3049 Full Paper Synthesis of New Unsymmetrical 4,5-Dihydroxy-2- imidazolidinones. Dynamic NMR Spectroscopic Study of the Prototropic Tautomerism in 1-(2-Benzimidazolyl)-3-phenyl-4,5- dihydroxy-2-imidazolidinone * Mehdi GhandiP P , Abolfazl Olyaei and Farshid Salimi School of Chemistry, University College of Science, University of Tehran, Tehran, Iran * P Author to whom correspondence should be addressed. E-mail: ghandi@khayam.ut.ac.ir; Tel.: (+98)-P 21 Fax: (+98)-21 Received: 28 September 2006; in revised form: 11 October 2006 / Accepted: 12 October 2006 / Published: 19 October 2006 Abstract: The acid-catalyzed cyclocondensation in refluxing acetonitrile of aqueous glyoxal with N-heteroaryl-N-phenylureas 4a-f (heteroaryl = 2-thiazolyl, 2-pyrimidinyl, 2-pyrazinyl, 2-pyridinyl, 3-pyridinyl and 2-benzimidazolyl) led to the formation of the corresponding 1-heteroaryl-3-phenyl-4,5-dihydroxy-2-imidazolidinones 5a-f. All the products were characterized by elemental and spectroscopic analyses. The free-energy ≠ barrier (∆GP P ) for prototropic tautomerism in 1-(2-benzimidazolyl)-3-phenyl-4,5- dihydroxy-2-imidazolidinone (5f) was determined by dynamic NMR studies to be 81 ± 2 -1 KJ molP P . Keywords: Dynamic NMR, N-Heteroaryl-N-phenylurea, 2-Imidazolidinone, Glyoxal. Introduction Synthesis of imidazolidines through the cyclocondensation of diami

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