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Updated: Jul 13, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
The methyl group as a source of structural diversity in heterocyclic chemistry: side chain functionalization of
Victor Mamane1, Emmanuel Aubert, Yves Fort
1Laboratoire 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
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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