The methyl group as a source of structural diversity in heterocyclic chemistry: side chain functionalization of picolines and related heterocycles |
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Authors: | Mamane Victor Aubert Emmanuel Fort Yves |
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Institution: | Laboratoire SRSMC, Equipe de Synthèse Organométallique et Réactivité, UMR CNRS-UHP 7565, Faculté des Sciences, Nancy-Université, BP 239, 54506 Vandoeuvre-Lès-Nancy, France. victor.mamane@sor.uhp-nancy.fr |
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Abstract: | 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. |
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