627812-08-2Relevant articles and documents
An Efficient Route to Pyrimidine Nucleoside Analogues by [4 + 2] Cycloaddition Reaction
Pearson, Morwenna S. M.,Robin, Aelig,Bourgougnon, Nathalie,Meslin, Jean Claude,Deniaud, David
, p. 8583 - 8587 (2007/10/03)
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 β-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).