An efficient route to pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction.
We report here an efficient synthesis for pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction. These compounds were obtained by convergent chemistry from glycosyl isothiocyanates 3a-f (pyranoses, furanoses, and dissaccharides) and diazadienium salt 5. In fact, diazapentadienium iodide 5 prepared from vinylthioamide 4 is an efficient intermediate in heterocyclic synthesis and reacts with isothiocyanates 3a-f affording beta-D-uracil analogues 7a-f in good yields and with total regiocontrol. All compounds were fully characterized by IR, HRMS, and 13C and 1H NMR (COSY and HMQC).
Laboratoire de Synthèse Organique, UMR CNRS 6513, Faculté des Sciences et des Techniques, 2, Rue de la Houssinière 44322 Nantes 03, France.
Morwenna S M
MS
Pearson
Aélig
A
Robin
Nathalie
N
Bourgougnon
Jean Claude
JC
Meslin
David
D
Deniaud
D004187:Disaccharides / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D017879:Isothiocyanates / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D011714:Pyrans / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D014498:Uracil / Q000737:chemistry
D004187:Disaccharides; D005663:Furans; D006027:Glycosides; D006571:Heterocyclic Compounds; D017879:Isothiocyanates; D011714:Pyrans; D011741:Pyrimidine Nucleosides; D014498:Uracil