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).
Pearson
Morwenna S M
MS
Laboratoire de Synthèse Organique, UMR CNRS 6513, Faculté des Sciences et des Techniques, 2, Rue de la Houssinière 44322 Nantes 03, France.
Robin
Aélig
A
Bourgougnon
Nathalie
N
Meslin
Jean Claude
JC
Deniaud
David
D
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