The Synthesis of Amidine Derivatives of Imidazoline Nitroxides - A New Series of pH-Sensitive Spin Probes and Labels

M. Yu Balakirev; V. V. Khramtsov; T. A. Berezina; V. V. Martin; L. B. Volodarsky

doi:10.1055/s-1992-26343

Synthesis 1992; 1992(12): 1223-1225
DOI: 10.1055/s-1992-26343

short paper

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The Synthesis of Amidine Derivatives of Imidazoline Nitroxides - A New Series of pH-Sensitive Spin Probes and Labels

M. Yu. Balakirev^* , V. V. Khramtsov, T. A. Berezina, V. V. Martin, L. B. Volodarsky

^*Institute of Chemical Kinetics & Combustion, Novosibirsk 630090, Russia

Abstract

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A synthesis of amidine derivatives, 4-alkyl[aryl]amino-2,5-dihydro-2,2,5,5-tetramethylimidazol-1-yl oxides is described. The first step is a 1,3-dipolar cycloaddition of 2,5-dihydro-2,2,5,5-tetramethylimidazol-1-yl 1,3-dioxide with isocyanates or diisocyanates. Alkaline hydrolysis of the resulting 3-substituted 2,3,3a,4,5,6-hexahydro-4,4,6,6-tetramethyl-2-oxoimidazo[1,5-b][1,2,4]oxadiazol-5-yl oxides affords the corresponding amidines. The resulting spin probes and labels may be used for measuring the local pH values in the range 3.3-7.8 in biological systems.

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