Synthesis of nitrogen-bridged purine-like C-nucleosides from ethyl 2,5-anhydro-6-O-benzoyl-d-allonodithioate
Department of Chemical Engineering; Department of Chemistry
Ethyl 2,5-anhydro-6-O-benzoyl-d-allonodithioate (1) was coupled with aminomethyl- and hydrazino-azines to afford the title compounds. Specifically, 1 was coupled with 2-(aminomethyl)pyridine to afford 3-β-d-ribofuranosylimidazolo-[1,5-a]pyridine, with 2-hydrazinopyrazine to yield 3-β-d-ribofuranosyl-1,2,4-triazolo[4,3-a]pyrazine, and with 2-hydrazinopyrimidine to form a 3-substituted 1,2,4-triazolo[4,3-a]pyrimidine which underwent a Dimroth rearrangement to yield 2-β- d-ribofuranosyl-1,2,4-triazolo[1,5-a]pyrimidine. Finally, compound 1 was coupled with 2-hydrazino-4-hydroxy-6-methylpyrimidine to yield 7-methyl-3-β-d-ribofuranosyl- 1,2,4-triazolo[4,3-a]-5(8H)-pyrimidone.
El Khadem, H.,
Synthesis of nitrogen-bridged purine-like C-nucleosides from ethyl 2,5-anhydro-6-O-benzoyl-d-allonodithioate.
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