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Paper | Regular issue | Vol 78, No. 10, 2009, pp.2455-2466
Published online, 17th July, 2009
DOI: 10.3987/COM-09-11742
Synthesis of Isomeric Analogs of Azathioprine

Alicja Kowalska,* Krystian Pluta, and Kinga Suwińska

*Department of Organic Chemistry, The Medical University of Silesia, Jagiellonska 4, 41-200 Sosnowiec, Poland


The effective synthesis of isomeric analogs of azathioprine - 6-substituted derivatives of 7-methyl-2-(1-methyl-4-nitroimidazol-5-ylthio)purines (2), (4) and (6-8) has been worked out using different reactivity of the imidazolylthio groups in 7-methyl-2,6-di(1-methyl-4-nitroimidazol-5-ylthio)purine (1) towards selected reagents. X-Ray analysis of compound (1) showed an unusual conformation of the imidazolylthio groups.