950993-49-4Relevant articles and documents
The methyl group as a source of structural diversity in heterocyclic chemistry: Side chain functionalization of picolines and related heterocycles
Mamane, Victor,Aubert, Emmanuel,Fort, Yves
, p. 7294 - 7300 (2008/02/11)
(Chemical Equation Presented) The reaction of 2-picoline at the methyl group with NDA and KDA followed by dimethyldisulfide trapping furnished, respectively, dithioacetals and trithioortho esters with high selectivity. The method was successfully applied to other methyl-substituted pyridines, quinolines, and pyrazines. Dithioketals were prepared by a one-pot procedure involving the reaction of metalated 2-picoline with 2 equiv of dimethyldisulfide followed by in situ trapping with a second electrophile. All of the generated thio-substituted compounds were efficiently transformed in presence of mercury salts or under oxidizing conditions to other functional groups comprising aldehydes, ketones, ketals, thiol esters, orthoesters, and esters.