354113-40-9Relevant academic research and scientific papers
Dimetalation of pyrazines. A one-pot synthesis of multisubstituted pyrazine C-nucleosides
Liu,Wise,Townsend
, p. 4783 - 4786 (2007/10/03)
As a part of our efforts to pursue direct, convergent, and concise methodologies for the synthesis of pyrazine C-nucleosides, we have successfully established a sequential dilithiation-addition method, which allows one to introduce two different functional groups to a pyrazine ring in a onepot fashion. 2,6-Dichloropyrazine was dilithiated at -100 °C and then allowed to react with an electrophile, such as bromine, iodine, or disulfides, followed by a reaction with a protected ribonolactone to afford C-nucleosides. After reduction and deprotection, tetrasubstituted pyrazine C-nucleosides, including 2,6-dichloro-3-iodo-5-(β-D-ribofuranosyl)pyrazine and 2-bromo-3,5-dichloro-6-(β-D-ribofuranosyl)pyrazine, were obtained. A tandem reaction sequence occurred when disulfides were used, resulting in the formation of 5,6-bis-methylthio-2-chloro-3-(β-D-ribofuranosyl)pyrazine and 6-(β-D-ribofuranosyl)-2,3,5-tris-phenylthiopyrazine.
