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DOI: 10.1055/s-0028-1083156
A Novel, Simple Cyclocondensation Reaction Towards Glycosyl Triazines
Publication History
Received
11 June 2008
Publication Date:
25 September 2008 (online)


Abstract
Sugars bearing an isothiocyanate moiety at C-1 react with diazadienium iodide to afford glycosyl triazines that represent, through an easy cyclocondensation reaction step, a flexible entry to different nucleoside analogues. We herein demonstrate that this [4+2] cycloaddition reaction occurs with total regiocontrol and good yields. Subsequent transformation of the thiocarbonyl into a carbonyl, and nucleophilic substitution of the methylsulfanyl group by ammonia, yields the 5-azacytidine analogues. All compounds were fully characterised by IR, HRMS, and ¹³C and ¹H NMR (COSY, HMBC and HMQC).
Key words
nucleosides - triazines - cycloaddition - 5-azacytidine - heterochemistry