335593-90-3

Upstream product

• 335593-89-0 2-(N,N-dimethylaminomethyleneamino)-5-formyl-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine 
• 335593-87-8 (6S)- and (6R)-6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3-(2H,6H)iminosemicarbazone 
• 335593-88-9 2-amino-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine 
• 121701-32-4 6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3<2H,6H>-one 
• 335593-94-7 (E)-2-amino-5-hydroxyiminomethyl-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine 

Relevant academic research and scientific papers

Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin

Syntheses of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides are reported. Treatment of pyranulose glycoside with aminoguanidine in acetic acid gave the corresponding semicarbazone in 96% yield. The ring transformation of the semicarbazone in dioxane afforded a 51% yield of 2-amino-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl) pyrrolo[2,1-f][1,2,4]triazine. Vilsmeier formylation of the pyrrolotriazine gave the major product, 5-formylpyrrolo[2,1-f][1,2,4]triazine, in 69% yield. The aldehyde was treated with hydroxylamine hydrochloride in methanol to give aldoximes. Dehydration of aldoxime with trifluoromethanesulfonic anhydride and triethylamine in dichloromethane afforded 5-cyanopyrrolo[2,1-f][1,2,4]triazine in 44% yield. Conversion of the nitrile to the deprotected amide, 2-amino-7-(β-D-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine-5- carboxamide, was accomplished in 96% yield on treatment with 30% H2O2 in ethanol for 1 day at room temperature. Debenzoylation with sodium hydroxide solution produced deprotected C-nucleosides.