5-Endo-dig electrophilic cyclization of alpha-alkynyl carbonyl compounds: synthesis of novel bicyclic 5-iodo- and 5-bromofuranopyrimidine nucleosides.
5-Endo-dig electrophilic cyclization of 5-alkynyl-2'-deoxyuridines with N-iodosuccinimide or N-bromosuccinimide in acetone at room temperature gives 3-(2'-deoxy-beta-D-ribofuranosyl)-5-halo-2,3-dihydrofuro[2,3-d]pyrimidin-2-ones that usually precipitate from the reaction mixture (86-74%).
Rao
Meneni Srinivasa
MS
Department of Chemistry, Oakland University, 2200 N. Squirrel Road, Rochester, Michigan 48309-4477, USA. dembinsk@oakland.edu
Esho
Noor
N
Sergeant
Craig
C
Dembinski
Roman
R
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001966:Bromine; D007202:Indicators and Reagents; D008968:Molecular Conformation; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D001643:Bridged Bicyclo Compounds; D007202:Indicators and Reagents; D011741:Pyrimidine Nucleosides; D001966:Bromine