4861-77-2Relevant academic research and scientific papers
New Simple Polymeric Supports with Hydrazone Linkers for Solid-Phase Synthesis of Ketones and Primary Amines
Lazny, Ryszard,Nodzewska, Aneta,Wolosewicz, Karol
, p. 2858 - 2864 (2007/10/03)
The preparation of new solid supports with hydrazine anchoring groups and their application to solid-phase synthesis of ketones and primary amines are described. The supports were used for immobilization of ketones, 4-tert-butylcyclohexanone, pentan-3-one, acetone, N-methylpiperidone, N-benzylpiperidone, and tropinone in the form of their hydrazones. The polymer-supported hydrazones were subjected to deprotonation/alkylation procedure (LDA/RX) once or twice. The resulting alkylated products were cleaved off the solid support on treatment with trifluoroacetic acid in tetrahydrofuran providing α-alkylated or α,α′-bisalkylated ketones or were subjected to reductive cleavage with borane in tetrahydrofuran to give β-alkylated or β,β′-bisalkylated primary amines.
Application of piperazine-derived hydrazone linkers for alkylation of solid-phase immobilized ketones
Lazny, Ryszard,Michalak, Michal
, p. 1931 - 1934 (2007/10/03)
The preparation and application of three new solid supports with piperazine-derived hydrazine anchoring groups are described. The supports were used for immobilization of ketones. The ketones: cyclohexanone, 4-tert-butylcyclohexanone, 3-pentanone and tropinone, which were bound to polymers in the form of their hydrazones, were deprotonated with LDA and alkylated with propyl iodide or benzyl bromide. The resulting alkylated products were cleaved off the solid support on treatment with trifluoroacetic acid in dichloromethane. Linkers with 6- and 3-carbon atom spacers gave better results than the simple N-aminopiperazine linker.
