A short, efficient synthesis of substituted uracil: An indane carbocyclic nucleoside

Citation
F. Fernandez et al., A short, efficient synthesis of substituted uracil: An indane carbocyclic nucleoside, SYNTHESIS-S, (2), 2001, pp. 239-242
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
2
Year of publication
2001
Pages
239 - 242
Database
ISI
SICI code
0039-7881(200102):2<239:ASESOS>2.0.ZU;2-I
Abstract
(+/-)-cis-1-(3-Hydroxymethyl-1-indanyl)-1,2,3,4-tetrahydropyrimidine-2,4-di one (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 pr epared from phenylsuccinic anhydride in four steps.