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Molecules 2006, 11(10), 768-775; doi:10.3390/11100768
Article

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

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Received: 28 September 2006 / Revised: 11 October 2006 / Accepted: 12 October 2006 / Published: 19 October 2006
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Abstract

The acid-catalyzed cyclocondensation in refluxing acetonitrile of aqueousglyoxal 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 thecorresponding 1-heteroaryl-3-phenyl-4,5-dihydroxy-2-imidazolidinones 5a-f. All theproducts were characterized by elemental and spectroscopic analyses. The free-energybarrier (∆GP≠ for prototropic tautomerism in 1-(2-benzimidazolyl)-3-phenyl-4,5-dihydroxy-2-imidazolidinone (5f) was determined by dynamic NMR studies to be 81 ± 2KJ molP-1
Keywords: Dynamic NMR; N-Heteroaryl-N'-phenylurea; 2-Imidazolidinone; Glyoxal. Dynamic NMR; N-Heteroaryl-N'-phenylurea; 2-Imidazolidinone; Glyoxal.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Ghandi, M.; Olyaei, A.; Salimi, F. 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. Molecules 2006, 11, 768-775.

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