77049-72-0Relevant academic research and scientific papers
A novel, simple cyclocondensation reaction towards glycosyl triazines
Kikelj, Vincent,Julienne, Karine,Janvier, Pascal,Meslin, Jean-Claude,Deniaud, David
, p. 3453 - 3460 (2008)
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). Georg Thieme Verlag.
