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Article

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2012-03-14

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/53208

Pd-catalysed amidation of 2,6-dihalopurine nucleosides. Replacement of iodine at 0 ºC

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http://dx.doi.org/10.1016/j.tetlet.2012.01.012

Abstract

Pd-catalysed reactions of 2-Cl, 2-Br and 2-I derivatives of a 6-chloropurine nucleoside with benzamide have been compared, using Pd2dba3, Xantphos and Cs2CO3 in toluene, between 20 and 80 °C. The reactivity order was 2-I > 2-Br > 6-Cl ≫ 2-Cl. The 2-I substituent could be replaced even at 0 °C, under conditions disclosed here for the first time. On the other hand, the replacement of the chlorine atom at position 2 (2-Cl) required 110 °C.

Subject

Àcids nucleics, Compostos heterocíclics, Citotoxicitat per mediació cel·lular, Nucleòsids, Medicaments antineoplàstics

Subject (English)

Nucleic acids, Heterocyclic compounds, Cell-mediated cytotoxicity, Nucleosides, Antineoplastic agents

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Articles publicats en revistes (Química Inorgànica i Orgànica)

Citation

BOSCH HEREU, Lluís, et al. Pd-catalysed amidation of 2,6-dihalopurine nucleosides. Replacement of iodine at 0 ºC. Tetrahedron Letters. 2012. Vol. 53, num. 11, pags. 1358-1362. ISSN 0040-4039. [consulted: 10 of June of 2026]. Available at: https://hdl.handle.net/2445/53208

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