Intramolecular cyclisation reactions in aliphatic thymidine analogues series
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 223-227
- https://doi.org/10.1039/p19820000223
Abstract
The intramolecular cyclisation of 1-(2-hydroxy-3-iodopropyl)thymine (2) by means of silver acetate afforded 2,3-dihydro-3-hydroxy-7-methyl-4H,8H-pyrimido[2,1-b][1,3]oxazin-8-one (3). On the other hand treatment of 1-(3-O-p-tolylsulphonyl-2,3-dihydroxypropyl)thymine (7) with sodium methoxide effected transformations yielding 2,3-dihydro-2-hydroxymethyl-6-methyl-7H-oxazolo[3,2-a]pyrimidin-7-one (8), via the intermediary 1-(2,3-epoxypropyl)thymine (6). The 3′-O-methylsulphonyl-2,2′-(16) rather than 2′-O-methylsulphonyl-2,3′-anhydro-(19) structure was formed when 1-(2,3-dimethylsulphonyloxypropyl)thymine (12) was treated with sodium methoxide in methanol. In addition the mesyl derivative (16) was converted into 2-azidomethyl-(20) and 2-aminomethyl-(21) 2,3-dihydro-6-methyl-7H-oxazolo[3,2-a]pyrimidin-7-one.This publication has 0 references indexed in Scilit: