Partial hydrogenation of substituted pyridines and quinolines: a crucial role of the reaction conditions |
| |
Authors: | A Solladié-Cavallo M Roje A BaramV Šunji? |
| |
Institution: | a Département de Chimie Organique Fine, ECPM/Université Louis Pasteur, 67087-Strasbourg, France b Laboratory for Stereoselective Catalysis and Biocatalysis, Department of Organic Chemistry and Biochemistry, Ruder Boškovi? Institute, Bijeni?ka 54, 10000 Zagreb, Croatia |
| |
Abstract: | Hydrogenation of pyridyl and quinolyl compounds 2-substituted with a carbonyl group (1a-c and 2b,c) using PtO2 and 1 equiv. of HCl (conditions A) provides clean and total formation of the desired amino alcohol (hydrogenation of the heterocyclic ring and of the carbonyl) while under conditions B1 and/or B2 (concentrated HCl or pure CF3CO2H) the heterocyclic ring remains untouched and other aromatic parts are hydrogenated providing complex mixtures. When the heterocyclic ring is substituted by an alkyl group (quinaldine 3) conditions A provide mixtures while under conditions B2 (pure CF3CO2H) the benzene ring is cleanly hydrogenated leading to a pure product. |
| |
Keywords: | hydrogenation aminoalcohol arylpyridylketones arylquinolylketones quinaldines |
本文献已被 ScienceDirect 等数据库收录! |