Imidazolidin-1-oles, N-2-aminoethyl nitrones and 1,2,5-oxadiazinanes. A novel ring-chain tautomerism |
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Authors: | Necdet Co?kun Oktay Asutay |
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Institution: | a Uluda? University, Department of Chemistry, 16059 Bursa, Turkey b Nam?k Kemal University, Muratl? Vocational School, Department of Chemistry, Muratl?-Tekirda?, Turkey |
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Abstract: | Imidazolin-3-oxides 1 were reduced with NaBH4 in THF at reflux to give the corresponding 2,3,5-triarylimidazolidin-1-oles 2, which are proved to be in a ring-chain-ring tautomeric equilibrium with N-2-aminoethyl nitrones 3 and 3,5,6-triphenyl-1,2,5-oxadiazinanes 4. The ratios of the ring and chain form are determined by the substituent at the reaction centre and can be described by the equation logKX = ρσ+ + logKX=H. These are the first examples of a novel three-component ring-chain-ring tautomeric equilibrium characterized by a Hammett-type equation. The stability of the ring form was favoured by electron-withdrawing substituents. Treatment of the equilibrium mixture of 2, 3 and 4 with phenylisocyanate in refluxing toluene gives selectively the corresponding O-carbamoylated imidazolidines 5; cis-5 was shown to isomerize to trans-5 on heating. |
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Keywords: | Nitrones Rearrangement Imidazoline Imidazoline-3-oxides Ring-chain tautomers |
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