Decarboxylation of 5-amino-orotic acid and a Schiff base derivative by rhenium(V) |
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| Affiliation: | 1. Materials Science & Engineering Department, Golpayegan University of Technology, P.O. Box 8771765651, Golpayegan, Iran;2. Department of Chemistry, Faculty of Sciences, University of Guilan, P.O. Box 41335–1914, Rasht, Iran;3. Department of Applied Chemistry, Faculty of Pharmaceutical Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran;4. Department of Chemistry, Sharif University of Technology, Azadi Ave., P.O. Box 11155–3516, Tehran, Iran |
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| Abstract: | The reaction of 5-amino-orotic acid (H2aor) with trans-ReOBr3(PPh3)2] in 2-propanol produced the complex ReV(apd)Br(aor)(PPh3)2] (1, apd2 − = 5-imidopyrimidine-2,4-dione). The ligand apd2 − was formed by the decarboxylation of H2aor, and it is coordinated via the dinegative imido nitrogen only. The Schiff base derivative of H2aor, salicylimine-orotic acid {5-(2-hydroxy-benzylideneamino)-1,2,3,6-tetrahydro-2,6-dioxopyrimidine-4-carboxylic acid; H2sor}, was also decarboxylated in the reaction with trans-ReOI2(OEt)(PPh3)2] in ethanol to form ReIII(cor)I(PPh3)2]I (2, Hcor = 5-(2-hydroxybenzylideneamino)-pyrimidine-2,4(1H,3H)-dione). Decarboxylation of H2sor was not observed in its reaction with trans-ReOCl3(PPh3)2], which led to the isolation of ReOCl(sor)(PPh3)] (3), in which sor2 − is coordinated as a tridentate ligand as expected. Spectroscopic results and the X-ray crystal structures of compounds 1–3 are also presented. |
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