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Synthesis 2001; 2001(2): 0239-0242
DOI: 10.1055/s-2001-10811
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A Short, Efficient Synthesis of Substituted Uracil: An Indane Carbocyclic Nucleoside

Franco Fernández* , Xerardo García-Mera, Melvin Morales, José E. Rodríguez-Borges
  • *Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15706-Santiago de Compostela, Spain; Fax +00(34)81594912; E-mail: qoxgmera§usc.es
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Publication Date:
31 December 2001 (online)

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(±)-cis-1-(3-Hydroxymethyl-1-indanyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione (1) was synthesised in two steps and with an overall yield of 51% from (±)-cis-3-amino-1-indanylmethanol (4) and 3-ethoxy-2-propenoyl isocyanate (3). The isocyanate 3 was prepared in 76% overall yield by reacting silver cyanate with 3-ethoxy-2-propenoyl chloride (2), which was obtained in one pot from ethyl vinyl ether and oxalyl chloride. The aminoalcohol (4) was prepared from phenylsuccinic anhydride in four steps.

synthesis - antiviral agent - antineoplastic agent - carbocyclic nucleoside - uracil derivative