1385043-49-1Relevant articles and documents
Synthesis of new γ-lactones from preactivated monosubstituted pyrazines and TMS-ketene acetals
Garduno-Alva, Azucena,Ortega-Alfaro, M. Carmen,Lopez-Cortes, Jose G.,Chavez, Isabel,Barroso-Flores, Joaquin,Toscano, Ruben A.,Rudler, Henri,Alvarez-Toledano, Cecilio
, p. 469 - 482 (2012)
The double addition of bis(trimethylsilyl) ketene acetals (1a-1b, R 1 = CH3,-(CH2)5-) to 2-substituted pyrazines promoted by triflic anhydride leads to γ-lactones in a single step. A systematic study involving electron-withdrawing and electron-donating groups (R2 = CN, COOMe, PhCH=CH, Cl, Me, OMe) in the pyrazine ring reveals a strong dependence of electronic effects on the regiochemistry of nucleophilic addition.