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Synthesis of phosphonate analogs of nucleotides with a 2,5-dihydro-1,2-oxaphospholene carbon skeleton

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Chemistry of Heterocyclic Compounds Aims and scope

Electrophilic halogenation of substituted diethyl [4-(6-amino-9H-purin-9-yl)-3-methylbuta-1,2-dien-1-yl]phosphonates proceeded as a heterocyclization involving the phosphoryl oxygen atom of the phosphonate fragment. The reaction products were 9-[(2-ethoxy-4-halo-5-methyl-2-oxido-2,5-dihydro-1,2-oxaphosphol-5-yl)methyl]-9H-purin-6-amines, a new type of phosphonate analog of nucleotides.

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Correspondence to V. K. Brel.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1826-1832, November, 2012.

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Brel, V.K. Synthesis of phosphonate analogs of nucleotides with a 2,5-dihydro-1,2-oxaphospholene carbon skeleton. Chem Heterocycl Comp 48, 1710–1715 (2013).

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