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Synthesis 2005(20): 3649-3653  
DOI: 10.1055/s-2005-918432
PAPER
© Georg Thieme Verlag Stuttgart · New York

Molecular Design of pH-Sensitive Spin Probes in the 2,3,4,6,7,8-Hexahydro­imidazo[1,5-a]pyrimidine Series with Different Lipophilic/Hydrophilic Properties­

Vadim K. Khlestkin*a, Vladimir V. Butakovb, Igor A. Grigor’eva, Andrey A. Bobkoc, Valerii V. Khramtsovc
a Vorozhtsov Institute of Organic Chemistry, Lavrent’eva prosp. 9, Novosibirsk, 630090, Russia
b Novosibirsk State University, Pirogova st. 2, Novosibirsk, 630090, Russia
c Institute of Chemical Kinetics and Combustion, Institutskaya st. 3, Novosibirsk, 630090, Russia
Fax: +7(3832)307752; e-Mail: vadim@nioch.nsc.ru;
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Publication History

Received 6 April 2005
Publication Date:
25 October 2005 (online)

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Abstract

New pH-sensitive spin probes - 2,3,4,6,7,8-hexahydro­imidazo[1,5-a]pyrimidines - were synthesized by the reaction of 4-amino-2,5-dihydro-2,2,5,5-tetramethyl-1H-imidazol-1-oxyl with aminomethylated α,β-unsaturated carbonyl methiodides or hydrochlorides. Introduction of hydrophilic (COOH) or lipophilic (C10H21) groups in the aminomethylated compounds allowed the synthesis of pH-sensitive spin probes with different solubilities.

Key words

radicals - enone - Mannich bases - spin probes - amidine

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Crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC- 149032. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk].